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Date
8 reactions in Reaxys
2018-03-20 12h:52m:57s (EST)
O– HO
1. Query
S OO
N+
Search as: As drawn AND (IDE.XRN=3599663)
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2018-03-20 13:11:19
N+
S
HN
H N
H N
HN
S
OH O– HO
S OO
O–
N+ HO
S OO
H N
H N S
H N OH
H N S
Rx-ID: 8732938 View in Reaxys 1/8 Yield
Conditions & References in chloroform-d1, T= 20 °C , Equilibrium constant Lee, Dong Hoon; Lee, Kwan Hee; Hong, Jong-In; Organic Letters; vol. 3; nb. 1; (2001); p. 5 - 7 View in Reaxys
p-methoxybenzyl 7β-[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)(tertbutoxycarbonyl) (ethylthio)methoxy]imino]acetamido]-3chloromethyl-3-cephem-4-carboxylate
O–
N+ HO
S OO
Rx-ID: 24366084 View in Reaxys 2/8 Yield
Conditions & References 2 : EXAMPLE 2 STR31 STR35 After 1.68 g of 5-mercapto-4-carboxy-3-hydroxyisothiazole tripotassium salt was dissolved in 20 ml of water, 20 ml of methylene chloride, 3.91 g of tetra-n-butylammonium hydrogensulfate and 5.00 g of p-methoxybenzyl 7β-[(Z)-2-(2tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl) (ethylthio)methoxy]-imino]acetamido]-3-chloromethyl-3-cephem-4-carboxylate obtained in (i) were added to the solution at room temperature. Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5233035; (1993); (A1) English View in Reaxys
p-methoxybenzyl 7β-[(Z)-2-tritylamino-4-thiazolyl)-2-[[(R S)(tert-butoxycarbonyl)(methylthio)methoxy]imino]acetamido]-3chloromethyl-3-cephem-4-carboxylate
O–
N+ HO
S OO
Rx-ID: 24366085 View in Reaxys 3/8 Yield
Conditions & References 1 : EXAMPLE 1 STR18 STR22 After 848 mg of 5-mercapto-4-carboxy-3-hydroxyisothiazole tripostassium salt was dissolved in 10 ml of water, 10 ml of methylene chloride, 1.98 g of tetra-n-butylammonium hydrogensulfate and 2.28 g of p-methoxybenzyl 7β-[(Z)-2tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(methylthio)methoxy]imino]acetamido]-3-chloromethyl-3-cephem-4-carboxylate obtained in (i) were added to the solution at room temperature. Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5233035; (1993); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/5
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O
O
O
Cl
O S HN
N
Z N
O–
N+
N
O
HO NS H
H O
S OO
S
O O
Rx-ID: 24366086 View in Reaxys 4/8 Yield
Conditions & References 3.7 : EXAMPLE 3 STR41 (7) After 696 mg of 5-mercapto-4-carboxy-3-hydroxyisothiazole tripotassium salt was dissolved in 10 ml of water, 10 ml of methylene chloride, 1.62 g of tetra-n-butylammonium hydrogensulfate and 2.00 g of p-methoxybenzyl 7β-[(Z)-2-(2tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(phenylthio)methoxy]imino]acetamido]-3-chloromethyl-3-cephem-4-carboxylate obtained in (6) were added to the solution at room temperature. Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5233035; (1993); (A1) English View in Reaxys
O
O
O Cl
O O
S HN
N
N
Z N
N H
H
O
O
O S
O–
N+ HO
S OO
O
O
O
S O
Rx-ID: 24366087 View in Reaxys 5/8 Yield
Conditions & References 4.9 : EXAMPLE 4 STR54 (9) After 1.24 g of 5-mercapto-4-carboxy-3-hydroxyisothiazole tripotassium salt was dissolved in 20 ml of water, 20 ml of methylene chloride, 2.88 g of tetra-n-butylammonium hydrogensulfate and 4.79 g of p-methoxybenzyl 7β-[(Z)-2-(2tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(3,4-diacetoxyphenylthio)methoxy]imino]acetamido]-3-chloromethyl-3-cephem-4-carboxylate obtained in (8) were added to the solution at room temperature. After stirring at room temperature overnight, the methylene chloride phase was separated and the aqueous phase was extracted with methylene chloride twice. The organic layers were collected and washed with 10 ml of saturated sodium chloride aqueous solution. Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5233035; (1993); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/5
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O
O
O
Cl
O N
O
S
NH HN
N
Z N
H
O–
N+
S
HO
S OO
O S
O O
O O
Rx-ID: 24366088 View in Reaxys 6/8 Yield
Conditions & References 6.6 : EXAMPLE 6 STR72 (6) After 2.54 g of 5-mercapto-4-carboxy-3-hydroxyisothiazole tripotassium salt was dissolved in 100 ml of water, 50 ml of methylene chloride, 5.95 g of tetra-n-butylammonium hydrogensulfate and 8.8 g of crude p-methoxybenzyl 7β[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(4-acetoxyphenylthio)methoxy]imino]acetamido]-3chloromethyl-3-cephem-4-carboxylate previously obtained were added to the solution at room temperature. After stirring at room temperature overnight, the methylene chloride phase was separated and the aqueous phase was extracted with methylene chloride twice. The organic layers were collected and washed with saturated sodium chloride aqueous solution. Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5233035; (1993); (A1) English View in Reaxys
–N
S
O–
N+ N+
HO
S OO
Rx-ID: 2429565 View in Reaxys 7/8 Yield 83 %
Conditions & References With sulfuric acid in water, Time= 1h, T= 75 °C Dehmlow, Eckehard V.; Vehre, Burkhard; Broda, Witold; Synthesis; nb. 5; (1985); p. 508 - 509 View in Reaxys
2,2-dimethyl-4-(2'-hydroxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan
O–
N+ HO
S OO
Rx-ID: 25136360 View in Reaxys 8/8 Yield
Conditions & References 3.2 : EXAMPLE 3 (2) Charged in a 3-liter reaction vessel equipped with a reflux condenser, thermometer, dropping funnel and stirrer were 240 g of a 50percent aqueous solution of sodium hydroxide (120 g, i.e., 3.0 moles of sodium hydroxide), 460 g of hexane, 8.5 g (0.025 mole) of tetrabutyl ammonium hydrogensulfate, and 230 g (0.5 mole) of the 2,2-dimethyl-4-(2'hydroxy-3'-isostearoxy)propoxymethyl-1,3-dioxolan obtained in Procedure (1) of Example 3. Patent; Kao Soap Co., Ltd.; US4504464; (1985); (A1) English
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/5
2018-03-20 13:11:19
View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/5
2018-03-20 13:11:19