Ethyl chloroformate → S-(-)-Amisulpride

HRID 564746Notes

Reaction equation

HRID 564746 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=O.ClC(OCC)=O.[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[CH2:31][NH2:32])[CH3:25]>CC(C)=O>[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[CH2:31][NH:32][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])[C:10]([NH2:12])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:25]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 643457(S)-(-)-2-Aminomethyl-1-ethylpyrrolidineHCID 30182324-Amino-5-(ethylsulfonyl)-2-methoxybenzoic acid

Product 1

HCID 3055076S-(-)-AmisulprideYield 84.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

95 g of 2-methoxy-4-amino-5-ethylsulphonylbenzoic acid dissolved in 370 ml of acetone, in the presence of 37 g of trielthylamine, is treated with 40 g of ethyl chloroformate with 57 g of (S)-(−)-1-ethyl-2-aminomethylpyrrolidine. 115 g of (S)-(−)-N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-ethylsulphonylbenzamide is obtained (yield=84%).

Sources & evidence

ORD record
ord-96b7f2ade85f45a3a8892a757cb44293
Source dataset
uspto-grants-2001_01
Patent number
US06169094A

Reaction notes

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