Benzyl Alcohol → Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

HRID 1646302Notes

Reaction equation

HRID 1646302 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:8])(=[O:3])[CH3:2].[CH2:26](O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([S:4][CH2:5][CH:6]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O:15][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:14])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10215552Benzoic acid, 3-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]-

Product 1

HCID 15670217Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-benzoic acid prepared in Example 68-(b)-[1](0.3 g),4-dimethylaminopyridine (0.01 g) and benzyl alcohol (0.1 g) are dissolved in dichloromethane (25 ml), and thereto is added EDC·HCl (0.18 g), and the mixture is stirred at room temperature three nights. The reaction mixture is washed with saturated aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution and water in this order, dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by a silica gel column chromatography (eluant, chloroform) to give the title compound (0.26 g).

Workup

  1. washThe reaction mixture is washed with saturated aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution and water in this order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is purified by a silica gel column chromatography (eluant, chloroform)

Sources & evidence

ORD record
ord-2fee52c78d91462cacc57f6c499aec62
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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