Benzyl chloroformate → (2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

HRID 36537노트

반응식

HRID 36537 반응식
C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[NH2:16][C@@H:17]([CH2:21][C:22]#[N:23])[C:18]([OH:20])=[O:19].[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:25]1([CH2:24][O:31][C:32]([NH:16][C@@H:17]([CH2:21][C:22]#[N:23])[C:18]([OH:20])=[O:19])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 4397423-cyano-L-alanine

생성물 1

HCID 12771373(2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Bis (trimethylsilyl)trifluoroacetamide (9.4 mL, 35 mmol.) was added to a suspension of (αS)-amino-3-cyanopropanoic acid (2.0 g., 17.5 mmol.) in 10 mL of dry acetonitrile and the reaction mixture was stirred for 3 hours. Benzylchloroformate (2.5 mL, 17.5 mmol) was added, the reaction mixture was stirred overnight, concentrated in vacuo, and dissolved in ethyl acetate (200 mL). The organic solution was washed with water (2×) and brine, dried (Na2SO4), and concentrated in vacuo. Crystallization from isopropyl ether yielded 3.82 g. of the title A product.

후처리

  1. stirringthe reaction mixture was stirred overnight
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in ethyl acetate (200 mL)
  4. washThe organic solution was washed with water (2×) and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customCrystallization from isopropyl ether
  8. customyielded 3.82 g

출처 및 근거

ORD 기록
ord-ee7f8a7636b943b6be7f4ce24c5ab941
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414017

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