2-Isocyanato-Thiazole → {2-Phenyl-4-[(thiazol-2-ylamino)carbonylthio]benzoyl}-methionine methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[S:26]1[CH:30]=[CH:29][N:28]=[C:27]1[N:31]=[C:32]=[O:33]>C1COCC1>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([S:13][C:32]([NH:31][C:27]2[S:26][CH:30]=[CH:29][N:28]=2)=[O:33])=[CH:9][C:8]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
4
Procedure
A solution of 2-phenyl-4-mercaptobenzoyl-methionine methyl ester from example 12E or 12F (1.0 mmol) and the isocyanate prepared in example 29A (1.0 mmol) in THF is refluxed until TLC shows no thiol left. The solvent is then evaporated in vacuo, and the residue is purified by column chromatography on silica gel to give the title compound.