Phenylacetyl chloride → N-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylacetyl)-L-asparaginyl]amino]butyl]-L-proline tert.butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetyl chloride	HCID 7679	—
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-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylacetyl)-L-asparaginyl]amino]butyl]-L-proline tert.butyl ester	HCID 70041037	67.4%

Reaction Steps

In a manner analogous to that described in Example 21, from 223 mg of N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester, 77 mg of phenylacetyl chloride and 65 mg of diisopropylethylamine there were obtained 190 mg of N-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(phenylacetyl)-L-asparaginyl]amino]butyl]-L-proline tert.butyl ester as a white solid (from ethyl acetate/n-hexane): MS: m/e 567 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05620987
Source dataset	uspto-grants-1997_04
ORD ID	ord-2f933407793c405f8cf814700f77ec17
Source note	uspto-grants-1997_04