Potassium Cyanide → tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022669ノート

反応式

HRID 1022669 の反応式
[C-:1]#[N:2].[K+].[Cl:4][C:5]1[CH:6]=[C:7]([C@@H:12]2[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C@H:13]2[CH2:26]OS(C)(=O)=O)[CH:8]=[CH:9][C:10]=1[Cl:11].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:1]([CH2:26][C@H:13]1[C@H:12]([C:7]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=2)[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:14]1)#[N:2]

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 86663851tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate

生成物 1

HCID 66975920tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate収率 78.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Potassium cyanide (1.720 g) was added to a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (3 g) in DMF (30 ml), and the mixture was stirred at 80° C. overnight. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.00 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-08b5932f985c4639b3fbf19496c224fe
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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