Ethanol → Dicyclohexylamine

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[S:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[CH3:15][C:16](=[CH2:27])[C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18].[CH2:28](O)C>>[CH:26]1([NH:19][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:9][CH2:10]2)[CH2:28][CH2:21][CH2:20][CH2:24][CH2:25]1.[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([S:7][CH2:15][C@@H:16]([CH3:27])[C:17]([N:19]2[CH2:26][CH2:25][CH2:24][C@H:20]2[C:21]([OH:23])=[O:22])=[O:18])=[O:8])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12]

Participants

Reactant 3

HCID 702Ethanol

HCID 132083491-(2-Methylacryloyl)-L-proline

HCID 178514757HCID 178514757, compound

Product 2

HCID 7582Dicyclohexylamine

HCID 12893586HCID 12893586, compound

Procedure

5 g of 4-chloro-3-sulfamoyl-thiobenzoic acid is added slowly to a stirred solution of 3.6 g of 1-(2-methyl-2-propenoyl)-L-proline in 50 ml of ethanol at room temperature. The resulting mixture is stirred overnight and then concentrated under reduced pressure. To the residue are added ethyl acetate and water. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is treated in an analogous manner of Example 4 to give dicyclohexylamine salt of 1-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-L-proline as white crystalline powder, melting at 143°-146° C.