Benzyl mercaptan → 2-Benzylsulfanyl-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester

HRID 47822Notes

Reaction equation

HRID 47822 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5](O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2].[CH:32]1[CH:37]=[CH:36][C:35]([CH2:38][SH:39])=[CH:34][CH:33]=1>>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([S:39][CH2:38][C:35]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 7509Benzyl mercaptanHCID 698837723-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

Product 1

HCID 698844092-Benzylsulfanyl-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester

Procedure

Synthesized from 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester using a procedure analogous to that used for Example 50 and substituting benzylthiol as the nucleophile to give an approximate 1:1 mixture of ethyl and methyl ester as a clear film (58 mg, 95%).

Workup

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Sources & evidence

ORD record
ord-c27f4f61df394971ac1b20ed531d0237
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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