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

HRID 1589075Notes

Reaction equation

HRID 1589075 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45531d7704d7440c897e02e2cc22e7dd
Source dataset
uspto-grants-1993_06
Patent number
US05223516

Reaction notes

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