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

HRID 1022719ノート

反応式

HRID 1022719 の反応式
[C:1]([C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1)(=O)[NH2:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:1]([C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1)#[N:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66976321tert-butyl (6R,7R)-6-carbamoyl-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

生成物 1

HCID 66975079tert-butyl (6S,7R)-6-cyano-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate収率 49.2%

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 tert-butyl (6R,7R)-6-carbamoyl-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (437 mg) and triethylamine (0.344 ml) in THF (5.6 mL) was added trifluoroacetic anhydride (0.171 mL), and the mixture was stirred at 0° C. for 2 hr. Then, the mixture was stirred at room temperature for 1 hr, distilled water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (205 mg).

後処理

  1. stirringThen, the mixture was stirred at room temperature for 1 hr
  2. distillationdistilled water
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with distilled water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-41efa7c80a9e4f55987cfe04d6d68d65
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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