2-Isocyanato-1,3-thiazole → {2-Phenyl-4-[(thiazol-2-ylamino)carbonylthio]benzoyl}-methionine methyl ester

HRID 325225Notes

Reaction equation

HRID 325225 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]=1

Participants

4

Reactant 2

HCID 234362202-Isocyanato-1,3-thiazoleHCID 542379062-Phenyl4-mercaptobenzoyl-methionine methyl ester

Product 1

HCID 86586788{2-Phenyl-4-[(thiazol-2-ylamino)carbonylthio]benzoyl}-methionine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. waitleft
  2. customThe solvent is then evaporated in vacuo
  3. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-114a10d5267546c488346cf0bab35e70
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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