Water → (7RS)-4-benzyl-7-(3,4-dichlorophenyl)-7-[(4-methoxyphenoxy)methyl]-1,4-oxazepan-3-one

HRID 1022588ノート

反応式

HRID 1022588 の反応式
[CH2:1]([N:8]([CH2:13][CH2:14][C:15]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)([OH:26])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:14][C:15]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[O:26][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 66976486N-benzyl-2-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butyl]acetamide

生成物 1

HCID 66976203(7RS)-4-benzyl-7-(3,4-dichlorophenyl)-7-[(4-methoxyphenoxy)methyl]-1,4-oxazepan-3-one収率 87.3%

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 N-benzyl-2-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butyl]acetamide (7.41 g) in THF (741 mL) was added sodium tert-butoxide (1.37 g), and the mixture was stirred at 0° C. for 2 hr, and then stirred while warming to room temperature for 14 hr. To the reaction mixture was added water, and the mixture was concentrated. The concentrated residue was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.02 g).

後処理

  1. stirringstirred
  2. temperaturewhile warming to room temperature for 14 hr
  3. concentrationthe mixture was concentrated
  4. additionThe concentrated residue was diluted with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe obtained extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-85eff9a6f75c420cb9b00d12b1b96f97
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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