Sodium Hydroxide → 2-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid

HRID 2355059노트

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HRID 2355059 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([O:18]C)=[O:17])=[CH:14][N:15]=2)[CH2:7]1.[OH-].[Na+]>C1COCC1.CO>[F:24][C:2]([F:1])([F:25])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=2)[CH2:7]1

참가 물질

4

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HCID 14798Sodium HydroxideHCID 68452698Methyl 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylate

생성물 1

HCID 684517792-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of methyl 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylate (1.2 g, 3.2 mmol) and 1M aqueous NaOH (6.4 mL, 6.4 mmol) in THF-MeOH (1:1, 24 mL) was heated at 80° C. bath for 2 h. Volatile solvents were removed in vacuo. The residue was diluted with H2O, acidified with 1M HCl (7 mL) and extracted with EtOAc. The EtOAc extract was washed with H2O, dried (Na2SO4), concentrated and triturated with Et2O to give the title compound as white solid. 1H NMR (400 MHz, acetone-d6): δ 7.84 (s, 1 H), 7.67 (m, 2 H), 7.41 (d, 1 H), 7.17 (t, 1 H), 5.51 (s, 1 H), 3.95 (m, 1 H), 3.81-3.60 (m, 3 H), 2.60-2.40 (m, 2 H).

후처리

  1. customVolatile solvents were removed in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customtriturated with Et2O

출처 및 근거

ORD 기록
ord-8a572a0e42614b9c9b189786c2f82402
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754745B2

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