Sodium Hydroxide → 3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acid

HRID 1397302Notes

Reaction equation

HRID 1397302 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[S:13][CH:14]=2)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67324988Ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate

Product 1

HCID 393539643-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N NaOH (5 mL) was added to an ice-cooled solution of crude ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate (450 mg, 1.61 mmol) in MeOH (5 mL) and the solution was allowed to stir at room temperature for 1 h. Solvent was evaporated and the reaction mixture was diluted with water. The aqueous layer was washed with EtOAc and the pH of the aqueous solution was adjusted to ˜2 using 1N HCl. The organic product was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoic acid (320 mg, yield 79%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.29 (br s, 1H), 7.99-7.96 (m, 2H), 7.93 (s, 1H), 7.28-7.22 (t, J=9.0 Hz, 2H), 3.25-3.20 (t, J=7.1 Hz, 2H), 2.78-2.74 (t, J=7.1 Hz, 2H). MS (ESI) m/z: Calculated for C12H10FNO2S: 251.04. found: 252.2 (M+H)+.

Workup

  1. customSolvent was evaporated
  2. additionthe reaction mixture was diluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionThe organic product was extracted with EtOAc
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e40b7e4e2fb4080a6be832fcc7929fb
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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