Dicyclohexylcarbodiimide → 3-benzyloxycarbonylamino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719117Notes

Reaction equation

HRID 1719117 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(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[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

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 13533189N-benzyloxycarbonyl-S-(2-aminophenyl)-beta-phenylcysteine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of N-benzyloxycarbonyl-S-(2-aminophenyl)-β -phenylcysteine was mixed with 0.5 g of dicyclohexylcarbodiimide and 15 ml of N,N-dimethylformamide and the resulting mixture was stirred for 5 hours. After the mixture was concentrated under reduced pressure, 20 ml of ethyl acetate was added to the residue and the insoluble matter was removed. Thereafter, the solution was concentrated to obtain the desired compound, or 3-benzyloxycarbonylamino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one. The physical properties of this product agreed with those of the compound obtained in Example 2.

Workup

  1. concentrationAfter the mixture was concentrated under reduced pressure, 20 ml of ethyl acetate
  2. additionwas added to the residue
  3. customthe insoluble matter was removed
  4. concentrationThereafter, the solution was concentrated

Sources & evidence

ORD record
ord-b4bc7e11ab064d399a1b0c586fbae573
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

Loading…