2-Acetylthiomethyl-3-phenylbutanoic acid → HCID 10456727, compound

HRID 233374Notes

Reaction equation

HRID 233374 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH2:18]([O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][CH2:31][CH3:32])[NH2:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][CH2:31][CH3:32])[NH:28][C:7](=[O:9])[CH:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 100607782-Acetylthiomethyl-3-phenylbutanoic acidHCID 14083110HCID 14083110, compound

Product 1

HCID 10456727HCID 10456727, compoundYield 75%

Procedure

Using the procedure described in Example 60, but starting with 2-acetylthiomethyl-3-phenylbutanoic acid and norleucine benzyl ester, and after purifying by chromatography, eluting with a hexane/ethyl acetate (75:25 by volume) mixture, N-(2-acetylthiomethyl-1-oxo-3-phenylbutyl)norleucine benzyl ester is obtained in a 75% yield in the form of an oil, having the following characteristics: Rf =0.46 [hexane/ethyl acetate(6.5:3.5 by volume)].

Workup

  1. customafter purifying by chromatography
  2. washeluting with a hexane/ethyl acetate (75:25 by volume) mixture

Sources & evidence

ORD record
ord-10757274540740f4ac583d0c9cb22542
Source dataset
uspto-grants-1997_01
Patent number
US05591891

Reaction notes

Loading…