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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1590115Generated: November 1, 2026

Ethyl Acetate → N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester

https://huagongshe.com/reaction/1590115

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactanttert-butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 107447—
ReactantHCID 178419261HCID 178419261—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
ProductN-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl esterHCID 17850141972.7%

Reaction Steps

L-Phenylalanyl-L-histidine methyl ester dihydrobromide(1.75 g) is dissolved in a mixture of dimethylformamide (10 ml) and triethylamine(1.4 ml), and N-tert-butoxycarbonyl-L-phenylalanine succinimido ester (1.34 g) is added thereto. The mixture is stirred at room temperature overnight. Ethyl acetate is added to the mixture, and insoluble materials are filtered off. The filtrate is washed with an aqueous sodium bicarbonate solution, and an aqueous sodium chloride solution is added thereto. The precipitated crystals are washed with ethyl acetate and water and then dried to give N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester(1.5 g) as colorless crystals. Yield: 71.8%

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05202312
Source datasetuspto-grants-1993_04
ORD IDord-51fc25ae16d84677bb8aa91e5a6da399
Source noteuspto-grants-1993_04