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Water → tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-ethenyl-1,4-oxazepane-4-carboxylate

HRID 1022648
ノート
印刷プレビュー

反応式

HRID 1022648 の反応式
[CH2:1]([Li])CCC.CCCCCC.[Cl:12][C:13]1[CH:14]=[C:15]([C@H:20]2[C@H:26]([CH:27]=O)[O:25][CH2:24][CH2:23][N:22]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:21]2)[CH:16]=[CH:17][C:18]=1[Cl:19].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([C@H:20]2[C@H:26]([CH:27]=[CH2:1])[O:25][CH2:24][CH2:23][N:22]([C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[CH2:21]2)[CH:16]=[CH:17][C:18]=1[Cl:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 86663857tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylateHCID 178418244HCID 178418244、化合物

生成物 1

HCID 66974991tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-ethenyl-1,4-oxazepane-4-carboxylate

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-78 °C

実験手順

A suspension of methyltriphenylphosphonium bromide (3.59 g) in THF (30 mL) was cooled under nitrogen purging to −78° C., and 1.6 M n-butyllithium/hexane solution (5.79 ml) was added. The mixture was warmed to 0° C., and stirred for 20 min, and a solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate (2.89 g) in THF (50 ml) was added. After stirring at 0° C. for 20 min, and at room temperature for 2 hr, 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%-30%)) to give the title compound (1.10 g) as a colorless oil.

後処理

  1. temperatureThe mixture was warmed to 0° C.
  2. stirringAfter stirring at 0° C. for 20 min
  3. waitat room temperature for 2 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-30%))

出典と根拠

ORDレコード
ord-aec5be62a44e4c53b535f14fa2feb49f
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722662B2

反応ノート

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