Water → methyl 2-(3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-methylpropanoate

HRID 64453

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HRID 64453 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20]([O:24][Si](C)(C)C)=[C:21]([CH3:23])[CH3:22].CN(C=O)C.O>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[F-].[Zn+2].[F-].C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][C@H:8]([C:10]1[CH:11]=[C:12]([C:21]([CH3:23])([CH3:22])[C:20]([O:19][CH3:18])=[O:24])[CH:13]=[CH:14][CH:15]=1)[CH3:9])=[O:17])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-2회HCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

생성물 1

HCID 86713467methyl 2-(3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-methylpropanoate

시약·촉매·용매 3

HCID 10129912Zinc(II) fluoride촉매HCID 178418851HCID 178418851, 화합물촉매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 1 g of tert-butyl[(1S)-1-(3-bromophenyl)ethyl]carbamate, 18 mg of bis(tri-tert-butylphosphine)palladium (0), 180 mg of zinc fluoride, 1 ml of [(1-methoxy-2-methylpropa-1-en-1-yl)oxy](trimethyl)silane, and 10 ml of DMF was stirred at 80° C. overnight and at 100° C. for 5 hours. 25 mg of bis(tri-tert-butylphosphine)palladium (0) and 0.34 ml of [(1-methoxy-2-methylpropa-1-en-1-yl)oxy](trimethyl)silane were added thereto, followed by stirring at 80° C. for 3 days. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 281 mg of methyl 2-(3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-methylpropanoate.

후처리

  1. stirringby stirring at 80° C. for 3 days
  2. customa layer separation operation
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-647d358395324543b17b84fbbf089926
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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