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

HRID 1397302노트

반응식

HRID 1397302 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6e40b7e4e2fb4080a6be832fcc7929fb
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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