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

HRID 325226Notes

Reaction equation

HRID 325226 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.[C:26](Cl)(Cl)=[O:27].C1(C)C=CC=CC=1.[NH2:37][C:38]1[S:39][CH:40]=[CH:41][N:42]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[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:26]([NH:37][C:38]2[S:39][CH:40]=[CH:41][N:42]=2)=[O:27])=[CH:9][C:8]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 21552-AminothiazoleHCID 6371PhosgeneHCID 542379062-Phenyl4-mercaptobenzoyl-methionine methyl ester

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-phenyl4-mercaptobenzoyl-methionine methyl ester from example 12E or 12F (1 equivalent) in methylene chloride is added a solution of phosgene in toluene (1.0 equivalent) and p-dimethylaminopyridine (2.0 equivalents). When the reaction is judged complete by TLC analysis, the solvent is evaporated with toluene chasers. The thiochloroformate is reacted without further purification with 2-aminothiazol (1.0 equivalent) and triethylamnine (1.0 equivalent) in dichloromethane. When judged complete by TLC analysis, the reaction is taken up in ethyl acetate and washed with 1N HCl and brine, evaporated, and purified by chromatography on silica gel.

Workup

  1. customthe solvent is evaporated with toluene chasers
  2. washwashed with 1N HCl and brine
  3. customevaporated
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-e835753685ec4392b34e52bbf72f86a1
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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