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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1759716Generated: October 26, 2026

(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester → (1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-(3-methoxy-3-oxo-propyl)benzoyl]amino]-L-alaninate

https://huagongshe.com/reaction/1759716

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl esterHCID 15550489—
Reactant5-Bromo-2-(methylthio)benzo[d]oxazoleHCID 22495792—
CatalystDiacetyloxymercuryHCID 16683746—
Product(1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-(3-methoxy-3-oxo-propyl)benzoyl]amino]-L-alaninateHCID 6973340011.5%

Reaction Conditions

Temperature75 °C

Reaction Steps

A mixture constituted by 890 mg of 10-5, 620 mg of 5-bromo-2-methylthiobenzoxazole (prepared according to P1 but starting from 4-bromo-2-nitrophenol) and 350 mg of Hg(OAc)2 is heated for 2 hours at 75° C. then for 2 hours at 95° C. The cooled down medium is chromatographed eluting with a CH2Cl2/AcOEt mixture 82/18. 159 mg of expected product is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06838453B2
Source datasetuspto-grants-2005_01
ORD IDord-e67a84d2213346f387d660aea3079512
Source noteuspto-grants-2005_01