Triethylamine → (2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid

HRID 1780271Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:28][C@@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:30]([OH:34])[C:31]([OH:33])=[O:32]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:28][C@@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:30]([OH:34])[C:31]([OH:33])=[O:32])=[O:19])[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 4 °C

Procedure

2.26 g of the p-nitrophenyl ester of benzyloxycarbonyl-L-asparagine and 1.89 ml (13.6 mmol) of triethylamine were added, whilst ice-cooling, to a solution of 900 mg (3.9 mmol) of (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid hydrochloride in 15 ml of dimethylformamide, and the mixture was stirred at 4° C. for 2 days. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with 1N aqueous hydrochloric acid to cause crystallization. The crystals were collected by filtration and washed first with water and then with ethyl acetate, to give 1.52 g of the title compound as colorless crystals, melting at 225°-227° C.

Workup

customAt the end of this time, the solvent was removed by distillation under reduced pressure
additionthe resulting residue was mixed with 1N aqueous hydrochloric acid
customcrystallization
filtrationThe crystals were collected by filtration
washwashed first with water

Sources & evidence

ORD record: ord-80bc48ca84914f38adace5cab6faf32b
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629406

Reaction notes

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