N-benzyloxycarbonyl-S-(2-aminophenyl)cysteine → 3-benzyloxycarbonylamino-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719103Notes

Reaction equation

HRID 1719103 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=O)[CH2:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[C:22](=[O:24])[NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57289832N-benzyloxycarbonyl-S-(2-aminophenyl)cysteine

Product 1

HCID 133751053-benzyloxycarbonylamino-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

17.8 g of N-benzyloxycarbonyl-S-(2-aminophenyl)cysteine was dissolved in 250 ml of xylene and the resulting solution was heated under reflux for 4 hours. After the solvent was distilled off under reduced pressure, ether was added to the residue. The precipitated crystals were separated to obtain 12.1 g of the desired compound, or 3-benzyloxycarbonylamino-2,3-dihydro-1,5-benzothiazepin-4(5H)-one. Its melting point was 149°-151° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 4 hours
  3. distillationAfter the solvent was distilled off under reduced pressure, ether
  4. additionwas added to the residue
  5. customThe precipitated crystals were separated

Sources & evidence

ORD record
ord-35e37af03b4549c28624e0f3d3e4850c
Source dataset
uspto-grants-1985_09
Patent number
US04539151

Reaction notes

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