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

HRID 1026219ノート

反応式

HRID 1026219 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-10c0a04ef7084f16998ced29b0ee4f0e
出典データセット
uspto-grants-2014_05
特許番号
US08729102B2

反応ノート

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