Benzenepropanoyl chloride → N-[3(S)-[(N-hydrocinnamoyl-L-asparaginyl)amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Benzenepropanoyl chloride	HCID 64801	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester	HCID 70041604	—
Solvent	Ethyl acetate hexane	HCID 21226206	—
Product	N-[3(S)-[(N-hydrocinnamoyl-L-asparaginyl)amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester	HCID 70047934	66.4%

Reaction Steps

In a manner analogous to that described in Example 21, from 249 mg of N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester, 94 mg of hydrocinnamoyl chloride and 72 mg of diisopropylethylamine there were obtained 214 mg of N-[3(S)-[(N-hydrocinnamoyl-L-asparaginyl)amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester as a white solid (from ethyl acetate/n-hexane); MS: m/e 581 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05554756
Source dataset	uspto-grants-1996_09
ORD ID	ord-79f05e08f7214f5fbe1ef7b6d6f83da6
Source note	uspto-grants-1996_09