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

HRID 39136노트

반응식

HRID 39136 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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%). 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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea786f9f59e244f2becb8a33a32b256f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

반응 노트

불러오는 중…