Ammonia → 2-Amino-2-iminoethylcarbamate AcOH

HRID 1990751

Reaction equation

HRID 1990751 reaction equation
CC([O:5][C:6]([NH:8][CH2:9][C:10]#[N:11])=[O:7])(C)C.C([NH:15][C@H:16]([C:19]([OH:21])=[O:20])CS)(=O)C.N>CO>[NH2:15][C:10](=[NH:11])[CH2:9][NH:8][C:6](=[O:7])[O-:5].[CH3:16][C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 12035N-Acetyl-L-CysteineHCID 545844tert-butyl N-(cyanomethyl)carbamate

Product 1

HCID 1317278412-Amino-2-iminoethylcarbamate AcOHYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Boc-aminoacetonitrile (40.2 g, 257.4 mmol) and N-acetylcysteine (42.0 g, 257.4 mmol) were dissolved in methanol (300 mL) at 60° C. and ammonia was passed through for 18 h. The solvent was removed in vacuo. After ion exchange chromatography (Amberlite IRA-400 (AcOH)) and recrystallisation from acetone, 28.4 g (53%) of the sub-title compound was obtained as a white solid.

Workup

  1. customwas passed through for 18 h
  2. customThe solvent was removed in vacuo
  3. customAfter ion exchange chromatography (Amberlite IRA-400 (AcOH)) and recrystallisation from acetone

Sources & evidence

ORD record
ord-7cb4b35b7c9f42a59a85e231a3293f05
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Linked notes

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