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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1949629Generated: November 1, 2026

Trifluoroacetic acid → 4-(2-Amino-3-tert-butoxy-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

https://huagongshe.com/reaction/1949629

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant4-(3-tert-Butoxy-2-tert-butoxycarbonylamino-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl esterHCID 67409401—
SolventDichloromethaneHCID 6344—
Product4-(2-Amino-3-tert-butoxy-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl esterHCID 6740882299.5%

Reaction Conditions

Temperature0 °C

Reaction Steps

A solution containing crude 43 (340 mg, 0.53 mmol) in DCM (10 mL) was cooled to 0° C. TFA (3 mL) was added. After 2 h, the reaction mixture was quenched by the slow addition of cold, aqueous K2CO3. The reaction mixture was extracted with DCM and the resultant organic phase was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 283 mg of 44 as an amber-colored foam which was used without further purification. Mass spectrum, m/z [537.3] (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08399683B2
Source datasetuspto-grants-2013_03
ORD IDord-0e41e655ca784a19a5e91e4ad0d87468
Source noteuspto-grants-2013_03