Dicyclohexylcarbodiimide → Racecadotril

HRID 1981229Notes

Reaction equation

HRID 1981229 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH2:17]([O:24][C:25](=[O:28])[CH2:26][NH2:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:17]([O:24][C:25](=[O:28])[CH2:26][NH:27][C:7](=[O:9])[CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][S:4][C:1](=[O:3])[CH3:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 85570p-ToluenesulfonateHCID 409140Benzyl glycinateHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid

Product 1

HCID 107751Racecadotril

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred ice-cold solution of 2.85 g (12 mmoles) 3-acetylthio-2-benzylpropanoic acid in 20 ml THF are successively added a mixture of 4.04 g (12 mmoles) glycine benzyl ester p.tosylate and 1.71 ml triethylamine in 20 ml CHCl3, a solution of 1.83 g (12 mmoles) HOBT in 15 ml THF, and a solution of 2.63 g (12.8 mmoles) DCC in 10 ml CHCl3.

Sources & evidence

ORD record
ord-7ad4005a1dfb4582a682e0ffc756d27f
Source dataset
uspto-grants-1985_04
Patent number
US04513009

Reaction notes

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