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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1671701Generated: October 31, 2026

Sodium Hydroxide → (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

https://huagongshe.com/reaction/1671701

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantCitrateHCID 31348—
ReactantAmmonium SulfateHCID 6097028—
ReactantEthyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylateHCID 10267979—
SolventDimethyl SulfoxideHCID 679—
Product(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideHCID 994491648%

Reaction Steps

5.0 g of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide were dissolved in 100 g of dimethylsulfoxide and thereto, 100 g of 0.05 mol/L citrate buffer solution (pH 4.4) were added, followed by adjusting pH value of the resultant mixture to 6.5 with a 5% sodium hydroxide aqueous solution. Thereto, 0.28 mL of esterase (PLE (2.7 kU/mL); manufactured by BioCatalytics, Inc., ammonium sulfate suspension) were added and the resultant mixture was stirred at 25° C. for 78 hours, followed by analyzing quantitatively the reaction mixture. As a result, in the reaction mixture, 2.4 g (quantitative yield: 48.6%) of (R)-2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide having an optical purity of 97-5% e.e. were contained

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07994342B2
Source datasetuspto-grants-2011_08
ORD IDord-1d3648cab4ec4799a02fa82aadd1515a
Source noteuspto-grants-2011_08