Water → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate

HRID 1022808ノート

反応式

HRID 1022808 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16](OC)=[O:17])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:27]([Mg]Br)=[CH2:28].[CH2:31]1COC[CH2:32]1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16]([OH:17])([CH:27]=[CH2:28])[CH:31]=[CH2:32])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 962WaterHCID 866638784-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylateHCID 178420667HCID 178420667、化合物

生成物 1

HCID 66976741tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylate (2.86 g) in THF (30 mL) was added 1.0 M vinylmagnesium bromide/THF solution (15.6 ml) under ice-cooling. The mixture was stirred at 0° C. for 20 min under nitrogen purging, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.31 g) as a colorless oil.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

出典と根拠

ORDレコード
ord-1382898bd28248b1a729ee2155e8deaf
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

反応ノート

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