2-Aminothiophenol → N-benzyloxycarbonyl-S-(2-aminophenyl)cysteine

HRID 1719101Notes

Reaction equation

HRID 1719101 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[CH2:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16][S:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 4674477Z-dehydro-Ala-OH

Product 1

HCID 57289832N-benzyloxycarbonyl-S-(2-aminophenyl)cysteineYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23 g of α-benzyloxycarbonylaminoacrylic acid and 30 g of 2-aminobenzenethiol were dissolved in 20 ml of ethanol, and the resulting mixture was stirred at room temperature for an hour. After the solvent was distilled off, ether was added to the residue so as to cause crystallization. The precipitated crystals were separated by filtration and washed with ether to obtain 17.8 g of the desired compound. Its melting point was 150°-151° C.

Workup

  1. distillationAfter the solvent was distilled off
  2. additionether was added to the residue so as
  3. customcrystallization
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-c8d3c246ed8b402ebc4fc361dd0d0feb
Source dataset
uspto-grants-1985_09
Patent number
US04539151

Reaction notes

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