Hydroxylamine → HCID 178472246, 화합물

HRID 75726

반응식

HRID 75726 반응식
[C:1]([C:3]1([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][C:6]([F:11])([CH2:9][OH:10])[CH2:5][CH2:4]1)#[N:2].[NH2:23][OH:24].[C:25]([C:32]([O:34][CH2:35][CH3:36])=[O:33])#[C:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CCO>[CH2:15]([O:14][C:13]([NH:12][C:3]1([C:1](=[NH:2])[NH:23][O:24][C:25](=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:8][CH2:7][C:6]([F:11])([CH2:9][OH:10])[CH2:5][CH2:4]1)=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 787HydroxylamineHCID 69803Diethyl acetylenedicarboxylateHCID 67977046HCID 67977046, 화합물

생성물 1

HCID 178472246HCID 178472246, 화합물수율 60.2%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
80 °C

실험 절차

A flask was charged with benzyl 1-cyano-4-fluoro-4-(hydroxymethyl)cyclohexylcarbamate, Intermediate 33, (13.0 g, 42.4 mmol), EtOH (100 mL) and aqueous hydroxylamine (26.0 mL, 424 mmol). The reaction was stirred at 80° C. under nitrogen for 2 hours. The mixture was concentrated and the resulting residue diluted with CH2Cl2, washed with brine, dried (MgSO4) and the solvent evaporated to provide a colorless oil. The oil was dissolved in EtOH (100 mL) to which diethyl acetylenedicarboxylate (13.54 mL, 85 mmol) was added. The reaction was stirred under nitrogen for one hour. The solution was concentrated and the residue was dissolved in CH2Cl2 then purified by silica gel column chromatography eluting with hexane/ethyl acetate (0 to 100%). The appropriate fractions were combined and evaporated to give the title compound (13.01 g, 25.5 mmol, 60.2% yield)] as a light yellow syrup.

후처리

  1. concentrationThe mixture was concentrated
  2. additionthe resulting residue diluted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customto provide a colorless oil
  7. additionwas added
  8. stirringThe reaction was stirred under nitrogen for one hour
  9. concentrationThe solution was concentrated
  10. dissolutionthe residue was dissolved in CH2Cl2
  11. customthen purified by silica gel column chromatography
  12. washeluting with hexane/ethyl acetate (0 to 100%)
  13. customevaporated

출처 및 근거

ORD 기록
ord-84c4207b97494f619cee774f0d6465ba
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835411B2

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