Ethyl Acetate → t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

HRID 569755ノート

反応式

HRID 569755 の反応式
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[N:12]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][NH:17][C:16]1=[O:28])=[N+:13]=[N-:14].C(OCC)(=O)C>CN(C)C=O.O>[N:12]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][N:17]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:16]1=[O:28])=[N+:13]=[N-:14]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 140034353(S*)-Azido-6(R*)-phenylperhydroazepin-2-one

生成物 1

HCID 14003443t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

0.9 ml of t-butyl bromoacetate followed by 219 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, under a stream of nitrogen, to a solution of 1.05 g of 3(S*)-azido-6(R*)-phenylperhydroazepin-2-one (Isomer A) [prepared as described in Example 1(f)] in 10 ml of dimethylformamide, whilst ice-cooling. The mixture was stirred for 1.5 hours, and then ethyl acetate and water were added. The ethyl acetate layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography using a 1:4 by volume mixture of ethyl acetate and cyclohexane as eluent, to give 1.54 g of the title compound as crystals, melting at 119°-121° C.

後処理

  1. temperaturewhilst ice-cooling
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customThe residue was purified by silica gel column chromatography
  7. additionby volume mixture of ethyl acetate and cyclohexane as eluent

出典と根拠

ORDレコード
ord-fea1c6b223c245bfa5827ddd55dd5a4a
出典データセット
uspto-grants-1988_03
特許番号
US04734410

反応ノート

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