Ethanethiol → 3-{4-[2-(tert-Butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethylsulfanyl-propionic Acid Ethyl Ester

HRID 47823Notes

Reaction equation

HRID 47823 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].[Na].[CH2:33]([SH:35])[CH3:34]>>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([S:35][CH2:33][CH3:34])[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

4

Reactant 3

HCID 6343EthanethiolHCID 5360545SodiumHCID 698837723-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

Product 1

HCID 698844043-{4-[2-(tert-Butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethylsulfanyl-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 the sodium salt of ethanethiol as the nucleophile to give an approximate 1:1 mixture of ethyl and methyl ester as a clear film (23 mg, 43%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-120af5db9851420fa573a4af83d2c3be
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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