Diethyl Ether → 3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid

HRID 725655Notes

Reaction equation

HRID 725655 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16].C(OCC)C>C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:1]([O:8][C:9]([NH:12][CH2:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 64956Beta-Aminoisobutyric Acid

Product 1

HCID 3042743-(((Benzyloxy)carbonyl)amino)-2-methylpropanoic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 41.7 ml of chloroformic acid benzyl ester (90%) in toluene is added to 25 g of 3-amino-2(R,S)-methylpropionic acid in 533 ml of 1N sodium hydroxide at 0° C. The reaction mixture is then stirred for 30 minutes at 0° C. After the addition of 400 ml of diethyl ether, the aqueous phase is removed and 140 ml of 4N hydrochloric acid are added. The crude title compound is obtained from the organic phase by extraction with diethyl ether: Rf (dichloromethane/methanol=8:2)=0.41.

Workup

  1. customthe aqueous phase is removed
  2. addition140 ml of 4N hydrochloric acid are added

Sources & evidence

ORD record
ord-fc361ff62aed4ddea9fce955975be3a7
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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