Hydrochloric Acid → (alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

HRID 55766

Reaction equation

HRID 55766 reaction equation
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[Li+].[OH-].Cl[C:15]([O:17][CH3:18])=[O:16].Cl>O>[CH3:18][O:17][C:15]([NH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6586Methyl chloroformateHCID 70134Phenylglycine, D-

Product 1

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (R)-2-amino-2-phenylacetic acid (14 g, 92.6 mmol) in water (250 mL) was added LiOH (14.8 g, 618.7 mmol) at 0° C. and the mixture was stirred for 15 minutes. To this solution, methyl chloroformate (17.9 mL, 231.5 mmol) was added drop wise and the mixture was stirred for 2 hours at 0° C. The mixture was then acidified until pH 1 with concentrated HCl. The mixture was extracted with EtOAc and the organic phase was concentrated in vacuum. The residue was dried overnight in vacuum, resulting in (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (11.8 g; 60.9 mmol).

Workup

  1. stirringthe mixture was stirred for 2 hours at 0° C
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic phase was concentrated in vacuum
  4. customThe residue was dried overnight in vacuum

Sources & evidence

ORD record
ord-01433eff02cb4e85957a7f07bbd728a8
Source dataset
uspto-grants-2016_09
Patent number
US09433609B2

Linked notes

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