Dicyclohexylcarbodiimide → 3-[2-(Benzyloxycarbonylamino)propionyl]-2,2-dimethyl-5-oxo-1-imidazolidineacetamide

HRID 256372Notes

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([CH3:28])[NH:22][CH2:21][C:20](=[O:23])[N:19]1[CH2:24][C:25]([NH2:27])=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:13])[C:14]([N:22]1[CH2:21][C:20](=[O:23])[N:19]([CH2:24][C:25]([NH2:27])=[O:26])[C:18]1([CH3:28])[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-5-oxo-1-imidazolidineacetamide (5.2 g) in 100 ml of dimethylformamide (DMF), a solution of dicyclohexylcarbodiimide (DCC) (6.2 g) in 50 ml of DMF was added dropwise during 15'. The suspension was stirred at 0° C. for 2 hours and at room temperature for additional 2 hours. The insoluble material was filtered off, the solvent was evaporated under reduced pressure, affording crude 3-[2-(benzyloxycarbonylamino)propionyl]-2,2-dimethyl-5-oxo-1-imidazolidineacetamide m.p. 206°-210° C. Into a solution of this compound (3 g) in methanol (100 ml) containing 5% palladium on charcoal (0.6 g) hydrogen was bubbled at 20° C. for 1.5 hours. Removal of catalyst and evaporation of the solvent gave a residue which was triturated with ethanol to afford the title compound, m.p. 196°-197° C.

Workup

filtrationThe insoluble material was filtered off
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-82aed7c04d9841b3bb196b74552d8365
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04703054

Reaction notes

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