Sodium Hydroxide → (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid

HRID 1366981Notes

Reaction equation

HRID 1366981 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([C:13]1[N:14]=[C:15]([CH3:25])[S:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:12].[OH-].[Na+]>CO.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[S:16][C:15]([CH3:25])=[N:14][C:13]=2[C:11]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[CH2:4][C:3]([OH:26])=[O:2])=[O:12])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66968203(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl ester

Product 1

HCID 23146320(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acidYield 82%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A stirring solution of (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl ester, D16 (4.00 g, 10.6 mmol) in methanol/water (75 ml/25 ml) was treated with sodium hydroxide (0.85 g, 21.3 mmol). The mixture was stirred for 16 h at room temperature. The methanol was removed in vacuo and the residue was diluted with water and extracted with diethyl ether (2×). The aqueous phase was acidified with 5N HCl and the product was extracted with ethyl acetate. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with pentane to afford the title compound as a white solid (3.10 g, 82%).

Workup

  1. customThe methanol was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (2×)
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-5e848200b6654c45b97a0af287735d39
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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