Ethanol → ethyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylate

HRID 1026219노트

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HRID 1026219 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:4][C:3]=1[F:20].C(N(CC)CC)C.[CH2:28]([OH:30])[CH3:29].CN([CH:34]=[O:35])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[C:15]([O:14][C:13]([NH:12][C@@H:10]([CH3:11])[CH2:9][O:8][C:5]1[CH:4]=[C:3]([F:20])[C:2]([C:34]([O:30][CH2:28][CH3:29])=[O:35])=[N:7][CH:6]=1)=[O:19])([CH3:18])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 702EthanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 86666267tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamate

생성물 1

HCID 67778422ethyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylate

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매

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온도
80 °C

실험 절차

Under a carbon monoxide atmosphere, a mixture of tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamate (500 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (135 mg), triethylamine (0.229 mL), ethanol (5 mL) and DMF (5 mL) was stirred at 80° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (402 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-10c0a04ef7084f16998ced29b0ee4f0e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729102B2

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