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

HRID 2355059ノート

反応式

HRID 2355059 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a572a0e42614b9c9b189786c2f82402
出典データセット
uspto-grants-2010_07
特許番号
US07754745B2

反応ノート

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