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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174262Generated: October 30, 2026

Hydrochloric Acid → tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate

https://huagongshe.com/reaction/1174262

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactantethyl (5S)-3-(4-bromobenzyl)-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-2-oxotetrahydro-3-furancarboxylateHCID 67406735—
SolventEthanolHCID 702—
SolventWaterHCID 962—
Producttert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamateHCID 8659881894.6%

Reaction Conditions

Temperature25 °C

Reaction Steps

A solution of the product from Example 92A (22.4 g) in ethanol (120 mL) was treated with LiOH monohydrate (8.0 g, 190.7 mmol) solution in water (30 mL) and the mixture was stirred at 25° C. for 16 hours. The mixture was cooled to 0° C., adjusted to pH 5 by addition of 4N HCl and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate in toluene (400 mL) was then heated at reflux for 18 hours, cooled and concentrated to give the title compound (18.4 g), which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834043B2
Source datasetuspto-grants-2010_11
ORD IDord-bca720b1212c459aba21c7687ab1d6f9
Source noteuspto-grants-2010_11