2-[(S)-(Diphenylmethyl)sulfinyl]acetamide [(S)-(+)-Modafinil] by Asch

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References A

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With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate in tetrachloromethane

T=20°C; 48 h; Title compound not separated from byproducts.;

Ternois, James; Guillen, Frederic; Plaquevent, Jean-Christophe; Coquerel, Gerard

Tetrahedron Asymmetry, 2007 , vol. 18, # 24 p. 2959 - 2964 Title/Abstract Full Text View citing articles Show Details

With bis(acetylacetonate)oxovanadium; 2,4-di-tert-butyl-6-((E)-(((1R,2S)-2hydroxy-1,2-diphenylethyl)imino)methyl)phenol; dihydrogen peroxide in chloroform

T=20°C; 3.5 h; optical yield given as percent eeenantioselective reaction; Hide Experimental Procedure

Stingl, Kerstin A.; Weiss, Katharina M.; Tsogoeva, Svetlana B.

Tetrahedron, 2012 , vol. 68, # 40 p. 8493 - 8501 Title/Abstract Full Text View citing articles Show Details

4.6. General procedure for the synthesis of (R)-modafinil-vanadium catalysis

General procedure: VO(acac)2 (2 mol percent) and ligand 6 or 10 (3 mol percent) were dissolved in CHCl3 (145 μL). The solution turned slightly green-brown after stirring for 60 min. 2-(Benzhydrylthio)acetamide (30 mg, 0.12 mmol) was added, followed by the addition of aqueous H2O2 (30percent, 1.2 equiv) in one portion. The reaction mixture was stirred at room temperature for a certain time (see Table 5, entries 2-7). The product was directly purified by column chromatography on silica gel (EtOAc). The isolated enantiomerically-enriched (R)-modafinil was identified through comparison of 1H NMR spectra with literature data (see Ref. 19). The enantiomeric excess of the product was determined by chiral HPLC analysis (Daicel Chiralpak AS, flow 0.9 mL/min, Hex/i-PrOH 60:40, 25 °C, 31 bar).

With NADP in isopropyl alcohol

T=25°C; pH=8; 20 h; Alkaline conditions; Catalytic behavior; enantioselective reaction; Hide Experimental Procedure

CODEXIS, INC.; Ang, Ee Lui; Alvizo, Oscar; Behrouzian, Behnaz; Clay, Michael; Collier, Steven; Eberhard, Ellen; Fu, Fan Jaslyn; Song, Shiwei; Smith, Derek; Widegren, Magnus; Wilson, Robert; Xu, Junye; Zhu, Jun

Patent: US9267159 B2, 2016 ; Location in patent: Page/Page column 58-63 ; Title/Abstract Full Text Show Details

HTP Assay of CHMO Polypeptides: (0203) Primary screening used to guide optimization was carried out in a 200 μL volume in 96-well plate high-throughput (HTP) assay protocol using cell lysates. The general HTP assay conditions were: 1-100 g/L substrate (i.e., compound (1a) or (1b)), 10-200 μL of clear cell lysate containing the engineered CHMO polypeptide, 0.05-1.0 g/L NADP cofactor, 1 g/L ketoreductase (KRED) polypeptide for cofactor recycling, 0.025-0.100 M phosphate or TEA buffer solution containing 3.5percent-10percent (v/v) IPA (and optionally, 1.5percent acetone or 10percent PEG200) co-solvent, pH 8-9, 25° C. reaction temperature and 20 h reaction time (with 200 rpm shaking). The HTP assay conditions were changed slightly over the different rounds of the directed evolution of the CHMO variant polypeptide disclosed in order to detect those variants most improved in enzyme properties. Table 4 shows the HTP assay conditions used to perform primary screening of those variant polypeptides whose improved properties were confirmed by SFP assay as summarized in Tables 2A and 2B. Rounds 1-6 assays used the amide substrate of compound (1a) and Rounds 7-16 assays used the acid substrate of compound (1b). HTP Assay Results: (0220) Representative results in the primary screening using the HTP assay for both the amide substrate (compound (10) and the acid substrate (compound (2a)) are shown below in Tables 7 and 8.

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59%

With ammonium hydroxide; ammonium chloride in methanol

T=20°C;

Cao, Jianjing; Prisinzano, Thomas E.; Okunola, Oluyomi M.; Kopajtic, Theresa; Shook, Matthew; Katz, Jonathan L.; Newman, Amy Hauck

ACS Medicinal Chemistry Letters, 2011 , vol. 2, # 1 p. 48 - 52 Title/Abstract Full Text View citing articles Show Details

54%

With ammonium hydroxide; ammonium chloride in methanol

T=20°C;

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details

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A: 0.05% B: 71.2% C: 0.03%

With aluminum oxide in methyl tert-butyl ether (MTBE); ethanol

T=0 - 78.5°C; Heating / reflux; Product distribution / selectivity; Hide Experimental Procedure

Gome, Boaz

Patent: US2009/48464 A1, 2009 ; Location in patent: Page/Page column 5 ; Title/Abstract Full Text Show Details

2; 4; 5; 6; 7:

A reaction mixture (350 g) containing 40 g of crude armodafinil in absolute ethanol (10 ml/g of crude armodafinil), after treatment with activated basic alumina (using the conditions of Example 1) were charged into a 1 liter stirred glass lab reactor. The stirrer was turned on and the reaction mixture was heated to reflux (78.5° C.). Then 240 ml of MTBE was added, which causes the reflux temperature to decrease to 65.8° C. Then the

reaction mixture was cooled to 61° C. At 61° C. the reaction mixture was seeded with milled crystals of armodafinil. The seeded reaction mixture was stirred at 60.8-61° C. for 10 minutes, and then cooled to 0° C. during 5 hr. The obtained seeded reaction mixture was stirred at 0.1° C. for additional 13 hr, and the product was isolated by vacuum filtration. The filter cake was washed with 40 ml of absolute ethanol, and then the wet product was dried under reduced pressure in a lab oven heated to 60° C. 32.1 g of armodafinil crystals was obtained (80.2percent yield w/w).The purity of the product was determined by HPLC, and the impurity R-MDF-DS was not detected or found within the limits of detection. The concentration of the R-MDF-DS in the starting R-MDF-crude was: 1.16percent (crude purity: 96.9percent, crystal purity: 99.8percent area as measured by HPLC). Example 4Treatment in 20 Volumes of Absolute Ethanol, and Crystallization of Crude Armodafinil from Absolute Ethanol/MTBE MixtureCrude armodafinil (40 g) and 800 ml absolute ethanol were charged into a 1 liter stirred glass lab reactor. The stirrer was turned on and the solution was heated to 58.4° C. At 58.4° C., the product was completely dissolved. The optical purity of the solution was tested, and then 8 g of activated basic alumina were charged. The solution was treated with activated basic alumina, and sampled after 1, 4, 5 hrs for optical purity determination. The solution was cooled to 0° C., and kept over-night. Then the solution was heated again to 58° C., and the used Alumina was separated by vacuum filtration. After cleaning the reactor with fresh absolute ethanol, the filtered solution was charged back. The solvent was evaporated at reduced pressure, and at a reactor temperature of: 42-63° C. (jacket temperature of 60-65° C.). When the volume of the solution in the reactor has been reduced to the ratio of: 10 volumes vs. crude armodafinil, the evaporation was stopped by increasing pressure to ambient with nitrogen. During the evaporation, since the volume of the solvent and the reactor temperature has been reduced, the product precipitated. The slurry was heated to reflux (78° C.), and after obtaining dissolution, 120 ml of MTBE were charged, which caused the reflux temperature to decrease to 72° C. Then the solution was cooled to 50° C. At 50° C. the solution was seeded with milled crystals of armodafinil. The seeded solution was stirred at 50° C. for 30 minutes, and then cooled to 0° C. during 5 hr. The obtained slurry was stirred at 0° C. for over-night.The product was isolated by vacuum filtration. The filter cake was washed with 40 ml of absolute ethanol, and then the wet product was dried under reduced pressure in a lab oven heated to 60° C. 30.2 g of dry armodafinil crystals was obtained (75.5percent yield).The optical purity of the product was determined by HPLC, and the concentration of the S-isomer in the sample is presented in Table No. 3, Sample 2.Example 5Treatment in 25 Volumes of Absolute Ethanol, and Crystallization of Crude Armodafinil from Absolute Ethanol/MTBE MixtureCrude armodafinil (40 g) and 1000 ml absolute ethanol were charged in to a 1 liter stirred glass lab reactor. The stirrer was turned on and the solution was heated to 53.2° C. At 53.2° C. the product was completely dissolved, and then 8 g of activated basic alumina were charged (using the conditions of Example 1). The solution was treated with activated basic alumina for 6 hrs and then the used alumina was separated by vacuum filtration. The separated alumina was washed with one volume of ethanol. Then the solution was cooled to 10° C., and kept over-night. Then the solution was heated again to 53° C. The solvent was evaporated at reduced pressure, and at a jacket temperature of 55-65° C. When the volume of the solution in the reactor has been reduced to the ratio of: 10 volumes vs. crude armodafinil, the evaporation was stopped by increasing the pressure to ambient with nitrogen. During the evaporation, since the volume of the solvent and the reactor temperature has been reduced, the product precipitated. The slurry was heated to reflux (76° C.), and after obtaining dissolution, 120 ml of MTBE was charged, which caused the reflux temperature to decrease to 72° C. Then the solution was cooled to 50° C. At 50° C., the solution was seeded with milled crystals of armodafinil. The seeded solution was stirred at 50° C. for 10 minutes, and then cooled to 0° C. during 1.5 hr. The obtained slurry was stirred at 0° C. for over-night. The product was isolated by vacuum filtration. The filter cake was washed with 40 ml of absolute ethanol, and then the wet product was dried under reduced pressure in a lab oven heated to 60° C. 31 g of dry armodafinil crystal was obtained (77.5percent yield).The purity of the product was determined by HPLC, and the concentration of the S-isomer is presented in Table No. 3, Sample 4.Example 6Purification by Crystallization of Crude Armodafinil from Ethanol/MTBE Mixture without Obtaining Complete Dissolution Before CoolingCrude armodafinil (40 g) and 1000 ml absolute ethanol (25 vol) were charged in to a 1 liter stirred glass lab reactor. The stirrer was turned on and the solution was heated to 52° C. At 52° C. the product was completely dissolved. The optical purity of the solution was tested, and then 8 g of activated basic alumina were charged. The solution was treated with activated basic alumina, and sampled after 1, 2.5, 5.5 hrs for optical purity determination. The used alumina was separated by vacuum filtration, washed with one volume of ethanol, and then the solution was cooled to 110° C., and kept over-night. Then the solution was heated again to 53° C. and sampled for optical purity determination. The solvent was evaporated at reduced pressure, and at a jacket temperature of 55-65° C. When the volume of the solution in the reactor has been reduced to the ratio of: 10 volumes vs. crude armodafinil (10 ml/g), the evaporation was stopped by increasing pressure to ambient with nitrogen. During the evaporation, since the volume of the solvent and the reactor temperature has been reduced, the product precipitated. Then, 120 ml of MTBE were charged, at a jacket temperature of 55° C. Then the solution was cooled to 0° C. during 2 hr. The obtained slurry was stirred at 0° C. for overnight.The product was isolated by vacuum filtration. The filter cake was washed with 40 ml of absolute ethanol, and then the wet product was dried under reduced pressure in a lab oven heated to 60° C. 30 g of dry armodafinil crystal was obtained (75percent yield).The purity of the product was determined by HPLC, and the concentration of the S-isomer in the sample is presented in Table No. 3, sample 3.Example 7Purification by Crystallization of Crude Armodafinil from Absolute Ethanol/MTBE Mixture without Dissolution and SeedingDry crude armodafinil (40 g) and 1000 ml of absolute ethanol (25 vol) were charged into a 1 liter glass stirred reactor. The mixer was turned on and the mixture was heated to a temperature of 55° C. to dissolve the armodafinil. 8 g of activated basic alumina were charged, and the mixture was stirred for 1 hr. Afterwards, 4 g of "Hyflo.(TM)." were charged, and then the solution was vacuum filtered. The concentration of BHSO in the clear solution was tested and found to be: 0.05percent. The filtrate was charged back in to the reactor, and the solvent was evaporated to 10 vol under reduced pressure, and at a maximum jacket temperature of 55° C. After completion of the evaporation, the reactor pressure was increased to ambient, and the slurry was heated to a temperature of 55° C. Then, 240 ml of MTBE was charged, and the reactor was stirred for 30 minutes at a temperature of 55° C. Afterwards, the slurry was cooled to a temperature of 0° C. during 5 hrs. The slurry was stirred at that temperature for overnight, and then the product was isolated by vacuum filtration, and the wet filter cake was washed with 40 ml of absolute ethanol (1 vol). The wet product was dried in a tray oven at reduced pressure and at a temperature of 60° C. 28.5 g of armodafinil crystal was obtained (71.2percent w/w). The product was tested, and it was found that the concentration of S-MDF is: 0.02percent (in the R-MDF-crude the concentration of S-MDF: 0.06percent). In addition, it was found that the impurity R-MDF-DS is not present (the concentration in R-MDF-crude: 1.74percent). Modafinic acid was present in <0.05percent. A

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A: 74.3% B: 0.03%

With aluminum oxide in methyl tert-butyl ether (MTBE); ethanol

T=-6.2 - 57°C; 12 h; Industry scale; Product distribution / selectivity; Hide Experimental Procedure

Gome, Boaz

Patent: US2009/48464 A1, 2009 ; Location in patent: Page/Page column 7 ; Title/Abstract Full Text Show Details

Dry crude armodafinil (28.8 kg) and absolute ethanol (597.7 kg) were charged into a 1 m3 glass lined stirred reactor. The mixer was turned on and the mixture was heated to a temperature of 55.5° C. to dissolve the armodafinil. The solution was circulated through a bed consisting of 5.8 kg activated basic alumina and 2.9 kg of "Hyflo.(TM)." (the bed was prepared separately at beginning of production of the batch).After 6 hrs of circulation, the concentration of BHSO was tested and found to be 0.17percent, after additional 2 hrs of circulation (total: 8 hrs of circulation), the solution was tested again and it was found that there is no BHSO in the solution (complete removal). Then the solution was filtered through the bed and through polishing filters into a second 1 m3 glass lined stirred reactor. Then the bed of Alumina/Hyflo.(TM). was washed with 56.9 Kg of absolute ethanol (2.5 L/kg of crude armodafinil), and the filtrate was collected into the second glass lined reactor. The stirrer in the second reactor was turned on, and the solution was cooled to 9.8° C., and then the pressure in the reactor was reduced to 54 mm Hg. The reactor jacket was heated gradually to 44.1° C. to obtain reflux. When reflux has been obtained the system was turned to distillation mode, and the distillate was collected. During the evaporation, 412 kg of ethanol were removed from the reactor at a pressure of 54-57 mm Hg, at a maximum jacket temperature of 50.9° C., and at a maximum reactor temperature of 26.2° C. The volume of solvent left in the reactor: 10.7 liter per kg of crude armodafinil. After completion of the evaporation, the reactor pressure has been increased to ambient, and the slurry was heated to a temperature of 53.2° C. Then, 191.8 kg of MTBE (9 vol) were charged, and the reactor was stirred for 2 hrs at a temperature of 57° C. Afterwards, the slurry was cooled to a temperature of -6.2° C. during 6 hrs. The slurry was stirred at that temperature for 2 hrs, and then the product was isolated by pressure filtration in a filter drier, and the wet filter cake was washed with 22.8 kg of absolute ethanol (1 vol). The washed filter cake was dewatered by mechanically squeezing, and then stirred dried at a pressure of 46-62 mm Hg, and at a jacket temperature of 60° C. The drying continued until the loss on drying of the product was: 0.04percent (tested by moisture analyzer at 90° C.). 21.4 kg of armodafinil crystal was obtained (74.3percent w/w).The product was tested, and it was found that the concentration of S-MDF is: 0.03percent (in the R-MDF-crude the concentration of S-

MDF: 0.05percent). In addition, it was found that the impurity R-MDF-DS is not present (the concentration in RMDF-crude: 1.23percent).

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TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.

Patent: WO2008/70143 A1, 2008 ; Location in patent: Page/Page column 9 ;

in dimethyl sulfoxide

T=100°C; 17 h; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

10:

A 20 ml vial equipped with a magnetic stirrer was charged with Armodafinil (0.5 g) and dimethylsulfoxide (5 ml). The suspension was heated to 100 C and was stirred for 17 hours to obtain yellow slurry and then cooled to 25 C. The sample was analyzed by HPLC to be 86.2percent of R and 13.8percent of S. TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.

Patent: WO2008/70143 A1, 2008 ; Location in patent: Page/Page column 9 ;

in N,N-dimethyl-formamide

T=100°C; 17 h; Heating; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

11:

A 20 ml vial equipped with a magnetic stirrer was charged with Armodafinil (0.5 g) and N,N-dimethylformamide (5 ml). The suspension was heated to 100 C and was stirred for 17 hours to obtain orange slurry and then cooled to 25 C. The sample was analyzed by HPLC to be 90.6percent by area of R and 9.4percent by area of S.

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With Bacillus subtilis var. niger IFO-3180 in N,N-dimethyl-formamide

T=28°C; 168 h;

Olivo, Horacio F.; Osorio-Lozada, Antonio; Peeples, Tonya L.

Tetrahedron Asymmetry, 2005 , vol. 16, # 21 p. 3507 - 3511 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / acetone / Heating 2: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 89 percent / Beauveria bassiana ATCC-7159 / dimethylformamide / 28 °C 2: 68 percent / Bacillus subtilis var. niger IFO-3180 / dimethylformamide / 168 h / 28 °C View Scheme

Olivo, Horacio F.; Osorio-Lozada, Antonio; Peeples, Tonya L.

Tetrahedron Asymmetry, 2005 , vol. 16, # 21 p. 3507 - 3511 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 7 steps 1.1: 99 percent / trifluoroacetic acid / 3 h / 20 °C 2.1: 99 percent / H2SO4 / Heating 3.1: H2SO4; 2-propanol; aq. H2O2 / methanol / 20 °C 4.1: 62.1 g / NaOH; H2O / ethanol / 1 h / 20 °C 5.1: (R)-(+)-α-methylbenzylamine / H2O / Heating 5.2: 17.0 g / aq. HCl / pH 2 6.1: 65 percent / K2CO3 / acetone / Heating 7.1: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 89 percent / Beauveria bassiana ATCC-7159 / dimethylformamide / 28 °C 2: 68 percent / Bacillus subtilis var. niger IFO-3180 / dimethylformamide / 168 h / 28 °C View Scheme

Olivo, Horacio F.; Osorio-Lozada, Antonio; Peeples, Tonya L.

Tetrahedron Asymmetry, 2005 , vol. 16, # 21 p. 3507 - 3511 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 6 steps 1.1: 99 percent / H2SO4 / Heating 2.1: H2SO4; 2-propanol; aq. H2O2 / methanol / 20 °C 3.1: 62.1 g / NaOH; H2O / ethanol / 1 h / 20 °C 4.1: (R)-(+)-α-methylbenzylamine / H2O / Heating 4.2: 17.0 g / aq. HCl / pH 2 5.1: 65 percent / K2CO3 / acetone / Heating 6.1: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details

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97%

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With ammonium hydroxide in methanol; chloroform

Rx-ID: 9833227 Find similar reactions

Osorio-Lozada, Antonio; Prisinzano, Thomas; Olivo, Horacio F.

Tetrahedron Asymmetry, 2004 , vol. 15, # 23 p. 3811 - 3815 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13306237 Find similar reactions

Multi-step reaction with 2 steps 1: 43.5 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH2Cl2

2: 97 percent / aq. ammonia / CHCl3; methanol View Scheme

Osorio-Lozada, Antonio; Prisinzano, Thomas; Olivo, Horacio F.

Tetrahedron Asymmetry, 2004 , vol. 15, # 23 p. 3811 - 3815 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1.1: (R)-(+)-α-methylbenzylamine / H2O / Heating 1.2: 17.0 g / aq. HCl / pH 2 2.1: 65 percent / K2CO3 / acetone / Heating 3.1: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 5 steps 1.1: H SO ; 2-propanol; aq. H O / methanol / 20 °C

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Rx-ID: 13520363 Find similar reactions

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058

2 2

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2.1: 62.1 g / NaOH; H2O / ethanol / 1 h / 20 °C 3.1: (R)-(+)-α-methylbenzylamine / H2O / Heating 3.2: 17.0 g / aq. HCl / pH 2 4.1: 65 percent / K2CO3 / acetone / Heating 5.1: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

Synthesize Find similar Multi-step reaction with 4 steps 1.1: 62.1 g / NaOH; H2O / ethanol / 1 h / 20 °C 2.1: (R)-(+)-α-methylbenzylamine / H2O / Heating 2.2: 17.0 g / aq. HCl / pH 2 3.1: 65 percent / K2CO3 / acetone / Heating 4.1: 54 percent / aq. NH4OH; NH4Cl / methanol / 20 °C View Scheme

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Rx-ID: 13540210 Find similar reactions

Prisinzano, Thomas; Podobinski, John; Tidgewell, Kevin; Luo, Min; Swenson, Dale

Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1053 - 1058 Title/Abstract Full Text View citing articles Show Details