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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2193553Generated: October 31, 2026

Water → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid

https://huagongshe.com/reaction/2193553

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantLithium hydroxide, monohydrateHCID 168937—
Reactant(3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl EsterHCID 67274345—
Reactant(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl EsterHCID 68420071—
SolventTetrahydrofuranHCID 8028—
Product(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic AcidHCID 68421821—

Reaction Conditions

Temperature40 °C

Reaction Steps

To a solution of 2.9 (3R, 4R) and (3S, 4S)-1-benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic acid ethyl ester (8.0 mmol) in 50 ml THF were added 671 mg lithium hydroxide mono hydrate (, 16 mmol) and 0.5 ml water. The solution was stirred at 40° C. and the reaction monitored by TLC. After 72 h the solvent was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and evaporated. The residue was crystallized from a dichloromethane/hexane mixture.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08329908B2
Source datasetuspto-grants-2012_12
ORD IDord-f406e256d96646acb6282da856e4a168
Source noteuspto-grants-2012_12