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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1852048Generated: October 31, 2026

Water → (R)-2-Amino-N-benzyl-3-methoxypropionamide

https://huagongshe.com/reaction/1852048

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethyl SulfateHCID 6497—
ReactantSodium HydroxideHCID 14798—
Reactanttert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamateHCID 46223140—
SolventDichloromethaneHCID 6344—
Product(R)-2-Amino-N-benzyl-3-methoxypropionamideHCID 10104501—

Reaction Conditions

Temperature-10 °C

Reaction Steps

Accordingly to a solution of the compound tert-butyl [(R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxoethyl]carbamate of Formula-XXI in dichloromethane, charged the phase transfer catalyst and cooled the reaction mass to −10° C. and charged dilute solution of sodium hydroxide. Maintaining the temperature at −10° C.-0° C. charged dimethyl sulfate and maintained the reaction under stirring for 3-5 hours. Charged water at the end of the reaction, stirred, separated the organic layer and extracted the aqueous layer with the dichloromethane. Combined the organic layer and acidified with concentrated hydrochloric acid. Charged water to the clear solution and stirred. Separated the aqueous layer and extracted the organic layer further with water. Combined the entire aqueous layer and adjusted the pH to 12 with aqueous sodium hydroxide solution. Extracted the aqueous layer with dichloromethane and separated the organic layer. Extracted the aqueous layer further with dichloromethane to ensure the complete extraction of the desired product. The organic layer is washed and concentrated to isolate the compound (2R)-2-amino-N-benzyl-3-methoxypropanamide of Formula-VIII.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957252B2
Source datasetuspto-grants-2015_02
ORD IDord-df53dc5bf3794719bb71ad92eaaedf65
Source noteuspto-grants-2015_02