Lithium hydroxide, monohydrate → 1-(2-Oxo-2,3-dihydro-1,3-benzoxazol-5-YL)cyclopropane-1-carboxylic acid

HRID 83700ノート

反応式

HRID 83700 の反応式
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14](=[O:16])[NH:13][C:12]=3[CH:17]=2)[CH2:7][CH2:6]1)=[O:4].O[Li].O>CO.O>[O:16]=[C:14]1[NH:13][C:12]2[CH:17]=[C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]3)[CH:9]=[CH:10][C:11]=2[O:15]1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 59129179Methyl 1-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)cyclopropanecarboxylate

生成物 1

HCID 591292471-(2-Oxo-2,3-dihydro-1,3-benzoxazol-5-YL)cyclopropane-1-carboxylic acid収率 84.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-cyclopropanecarboxylic acid methyl ester (1.9 g, 8.1 mmol) in MeOH (20 mL) and water (2 mL) was added LiOH.H2O (1.7 g, 41 mmol) in portions at room temperature. The reaction mixture was stirred for 20 hours at 50° C. MeOH was removed by evaporation under vacuum before water (100 mL) and EtOAc (50 mL) were added. The aqueous layer was separated, acidified with HCl (3 mol/L) and extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)cyclopropanecarboxylic acid (1.5 g, 84%). 1H NMR (DMSO, 400 MHz) δ 12.32 (brs, 1H), 11.59 (brs, 1H), 7.16 (d, J=8.4 Hz, 1H), 7.00 (d, J=8.0 Hz, 1H), 1.44-1.41 (m, 2H), 1.13-1.10 (m, 2H). MS (ESI) m/e (M+H+) 218.1.

後処理

  1. customMeOH was removed by evaporation under vacuum before water (100 mL) and EtOAc (50 mL)
  2. additionwere added
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum

出典と根拠

ORDレコード
ord-2d569bfa8e3643019ac4af29a427a62e
出典データセット
uspto-grants-2014_09
特許番号
US08846753B2

反応ノート

読み込み中…