Dicyclohexylcarbodiimide → N-(3-Acetylthio-2-methylpropanoyl)-N-(cyclopropyl)glycine t-butyl ester

HRID 127612Notes

Reaction equation

HRID 127612 reaction equation
[C:1]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:13]([S:16][CH2:17][CH:18]([CH3:22])[C:19](O)=[O:20])(=[O:15])[CH3:14].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[CH2:7][N:8]([C:19](=[O:20])[CH:18]([CH3:22])[CH2:17][S:16][C:13](=[O:15])[CH3:14])[CH:9]1[CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 20285435Tert-butyl 2-(cyclopropylamino)acetate

Product 1

HCID 20285433N-(3-Acetylthio-2-methylpropanoyl)-N-(cyclopropyl)glycine t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(cyclopropyl)glycine t-butyl ester (12 g, 0.0702 mol) and 3-acetylthio-2-methylpropionic acid (8.1 g, 0.050 mol) in methylene chloride (200 ml) chilled in an ice bath was added dicyclohexylcarbodiimide (14.4 g, 0.070 mol). The resulting mixture was stirred for sixteen hours at room temperature. The dicyclohexylurea was removed by filtration and washed with diethyl ether. Evaporation of the filtrate yielded the crude product as a pale yellow oil which was used without further purification.

Workup

  1. customThe dicyclohexylurea was removed by filtration
  2. washwashed with diethyl ether
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-c6470db822ca4c209362c947f6a1add4
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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