반응 #84044

ord-01433eff02cb4e85957a7f07bbd728a8

반응 방정식

Cl
HCl
COC(=O)Cl
methyl chloroformate
N[C@@H](C(=O)O)c1ccccc1
(R)-2-amino-2-phenylacetic acid
[Li+].[OH-]
LiOH
COC(=O)N[C@@H](C(=O)O)c1ccccc1
(R)-2-(methoxycarbonylamino)-2-phenylacetic acid
수율 65.8%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.STIRRINGthe mixture was stirred for 2 hours at 0° C
  2. 2
    추출The mixture was extracted with EtOAc
  3. 3
    농축the organic phase was concentrated in vacuum
  4. 4
    기타The residue was dried overnight in vacuum

실험 절차

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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09433609B2uspto-grants-2016_09