Water → 3-(4-{Methoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenyl)-propionic acid methyl ester

HRID 854569Notes

Reaction equation

HRID 854569 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[S:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH3:29])=[CH:8][C:7]=1[CH3:30].N1C=CC=CC=1.Cl[C:39]([O:41][CH3:42])=[O:40].O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:39]([O:41][CH3:42])=[O:40])[CH2:13][C:14]2[S:18][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:23][CH:24]=3)=[N:16][C:15]=2[CH3:29])=[CH:8][C:7]=1[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 694694953-(2-Methyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenyl)-propionic acid methyl ester

Product 1

HCID 694759133-(4-{Methoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenyl)-propionic acid methyl esterYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 3-(2-Methyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenyl)-propionic acid methyl ester (0.05 g, 0.11 mmol) and pyridine (0.027 mL, 0.33 mmol) in anhydrous CH2Cl2 (3 mL) is added methyl chloroformate (0.026 mL, 0.34 mmol) dropwise. The mixture is allowed to warm to RT overnight. Water is added, and the mixture is extracted with CH2Cl2. The combined organics are dried with MgSO4 and concentrated to yield the title compound (57 mg, quant.)

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialThe combined organics are dried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ebf1cecc7a244d2992fb017cfff6fc3f
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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