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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1759712Generated: November 4, 2026

tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate → (1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate

https://huagongshe.com/reaction/1759712

Reaction equation

Participants

RoleNameHCIDCharge
Reactanttert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 15512208—
Reactant5-Bromo-7-fluoro-2-(methylthio)-benzoxazoleHCID 22599490—
CatalystMercuric acetateHCID 15337—
Product(1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinateHCID 6988064840.5%

Reaction Conditions

Temperature100 °C

Reaction Steps

The mixture constituted by aminoester 4-2 (865 mg; 2.46 mmoles), 5-bromo-7-fluoro-2-(methylthio)-benzoxazole (804 mg; 3.07 mmoles) and mercury diacetate (437 mg) is agitated for 3 hours, under nitrogen and at 100° C. After cooling down, the medium is chromatographed eluting with a CH2Cl2/ethyl acetate mixture 95/5, 564 mg of expected product is obtained, which is repurified by recrystallizing from isopropyl oxide. 528 mg of purified product is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06838453B2
Source datasetuspto-grants-2005_01
ORD IDord-57cb84ae0b3540efbaee501e8b58cb22
Source noteuspto-grants-2005_01