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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 248817Generated: October 26, 2026

Benzoic Acid → Benzoyl-glycine-t-butyl ester

https://huagongshe.com/reaction/248817

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic AcidHCID 243—
Reactant4-MethylmorpholineHCID 7972—
ReactantIsobutyl chloroformateHCID 62365—
ReactantGlycine tert-butyl esterHCID 151417—
ReactantGlycine,n-(1-oxo-3-phenyl-2-propen-1-yl)-, methyl esterHCID 582979—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductBenzoyl-glycine-t-butyl esterHCID 11020853—

Reaction Conditions

Temperature0 °C

Reaction Steps

Following the same general procedure described previously for cinnamoyl-glycine-methyl ester, glycine-t-butyl ester. MCl (10.88 grams) was dissolved in dimethyl formamide (approximately 100 ml), cooled to 0° C. and treated with N-methylmorpholine (9.04 ml, 1 equivalent) followed immediately by a pre-cooled solution of benzoic acid (7.94 grams) in ethyl acetate (approximately 75 ml) which had been pre-activated by treatment with N-methylmorpholine (9.04 ml) followed by isobutyl chloroformate (8.4 ml) at -20° C. After work-up, benzoyl-glycine-t-butyl ester was obtained as a white solid which was used for the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05212158
Source datasetuspto-grants-1993_05
ORD IDord-4d01de82081c4a869f6b99e9d83ef640
Source noteuspto-grants-1993_05