Dicyclohexylcarbodiimide → 1-[2-(Benzyloxycarbonylamino)propanoyl]-2,2-dimethyl-4-imidazolidinone

HRID 256355

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:24])[NH:22][C:21](=[O:23])[CH2:20][NH:19]1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:13])[C:14]([N:19]1[CH2:20][C:21](=[O:23])[NH:22][C:18]1([CH3:24])[CH3:17])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, ice-cold solution of N-(benzyloxycarbonyl)alanine (6.7 g) and 2,2-dimethyl-4-imidazolidinone (3.42 g) in 100 ml of THF, a solution of DCC (6.2 g) in 50 ml of THF was added dropwise during 15 minutes. The suspension was stirred at 0° C. for 2 hours and at room temperature for an additional 2 hours. The insoluble material was filtered off. The solvent was evaporated under reduced pressure. Crystallization of the residue from isopropanol gave the title product as a white powder m.p. 170°-171° C.

Workup

filtrationThe insoluble material was filtered off
customThe solvent was evaporated under reduced pressure
customCrystallization of the residue from isopropanol

Sources & evidence

ORD record: ord-ffc6e9b5aa7b4d39a10ddd0dd34644a3
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04703054

Linked notes

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