2-Aminothiophenol → N-benzyloxycarbonyl-S-(2-aminophenyl)-beta-phenylcysteine

HRID 1719114Notes

Reaction equation

HRID 1719114 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[S:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH2:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 53972564alpha-Benzyloxycarbonylamino-beta-phenylacrylic acid

Product 1

HCID 13533189N-benzyloxycarbonyl-S-(2-aminophenyl)-beta-phenylcysteineYield 9.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g of α-benzyloxycarbonylamino-β-phenylacrylic acid and 10 g of o-aminobenzenethiol were mixed with 40 ml of ethanol and the resulting mixture was heated under reflux for 20 hours. After cooling to room temperature, the precipitated crystalline component was separated by filtration and washed with ethanol to obtain 2.7 g of crystals. This product decomposed at 198° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customthe precipitated crystalline component was separated by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-5cc14afe26ad451da63add060ddf1931
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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