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

HRID 64453

反応式

HRID 64453 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 10129912Zinc(II) fluoride触媒HCID 178418851HCID 178418851、化合物触媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-647d358395324543b17b84fbbf089926
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

関連ノート

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