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

HRID 1719115Notes

Reaction equation

HRID 1719115 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:28]([OH:30])=O)[CH:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[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:28](=[O:30])[NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][CH:13]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 13533189N-benzyloxycarbonyl-S-(2-aminophenyl)-beta-phenylcysteine

Product 1

HCID 134905083-benzyloxycarbonylamino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.7 g of the N-benzyloxycarbonyl-S-(2-aminophenyl)-β-phenylcysteine obtained in Example 1 was suspended in 60 ml of xylene and the resulting suspension was heated under reflux for 3 hours. Thereafter, the apparatus was cooled to room temperature. The precipitated crystals were separated by filtration and washed with ethanol to obtain 1.9 g of the desired compound.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 3 hours
  3. customThe precipitated crystals were separated by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-4773343e90b04d5b82769aa30bf90378
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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