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

HRID 1676355ノート

反応式

HRID 1676355 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67348734HCID 67348734、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8b2ca2844edb4e8587b0ddcc0f114e25
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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