Hydrochloric Acid → 3-(4-Fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid

HRID 1676355노트

반응식

HRID 1676355 반응식
[Li+].[OH-].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH:14]3[C:12]([C:16]([O:18]C)=[O:17])([CH2:13]3)[C:11]2=[O:20])=[CH:6][CH:5]=1.Cl>C1COCC1.O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH:14]3[C:12]([C:16]([OH:18])=[O:17])([CH2:13]3)[C:11]2=[O:20])=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67348734HCID 67348734, 화합물

생성물 1

HCID 673496483-(4-Fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid수율 88.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

LiOH (0.2 g, 8.4 mmol) was added into a suspension of methyl 3-(4-fluorophenyl)-2-oxo-3-aza-bicyclo[3.1.0]hexane-1-carboxylate (1.2 g, 4.8 mmol) in THF (20 mL) and water (1 mL). The reaction was allowed to stir for 1 hour. The reaction mixture was poured into water and neutralized with 1M HCl. The mixture was extracted with EtOAc, washed with brine, dried with Na2SO4, filtered and concentrated to afford the title compound (1 g, 79% yield) as a light brown solid. LRMS (APCI pos) m/e 235.9 (M+1). 1H NMR: (DMSO-d6, 400 MHz): δ 12.70 (br s, 1H), 7.57-7.62 (m, 2H), 7.17-7.23 (m, 2H), 4.06 (dd, 1H), 3.70 (dd, 1H), 2.50-2.56 (m, 1H), 1.76-1.81 (m, 1H), 1.29-1.33 (dd, 1H).

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8b2ca2844edb4e8587b0ddcc0f114e25
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003662B2

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