Methanol → HCID 57787068, compound

HRID 1009198Notes

Reaction equation

HRID 1009198 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11][C:12](=[O:26])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[S:8][CH:9]=1)=[O:4].CO.[OH-].[Na+]>O>[F:25][C:22]([F:23])([F:24])[O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:12]([NH:11][CH2:10][C:7]2[S:8][CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=2)=[O:26])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 57787057HCID 57787057, compound

Product 1

HCID 57787068HCID 57787068, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-{[2-(4-Trifluoromethoxy-phenoxy)-acetylamino]-methyl}-thiazole-4-carboxylic acid methyl ester (8.6 g, 22 mmol) was mixed with methanol (110 mL). NaOH (1.3 g, 33 mmol) was dissolved in water (110 mL) and added to the methanol solution. The reaction mixture was stirred for 12 hours. The mixture became homogenous after three hours. The methanol was removed in vacuo and the resulting slurry was acidified with 1 N HCl. The resulting slurry was extracted with EtOAc ×3. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was recrystallized from methanol to afford the title compound (7.1 g, 86%). 1H NMR (400 MHz, d6-DMSO): 9.08 (t, 1H), 8.33 (s, 1H), 7.31 (d, 2H), 7.06 (d, 2H), 4.63 (s, 2H), 4.61 (d, 2H); MS (ESI-LCMS) for C14H12F3N2O5S: 377 (MH+).

Workup

  1. waitThe mixture became homogenous after three hours
  2. customThe methanol was removed in vacuo
  3. extractionThe resulting slurry was extracted with EtOAc ×3
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-adf38d19b1b44eb0a712a4406a018184
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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