Pyridine → (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine

HRID 1464734ノート

反応式

HRID 1464734 の反応式
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C@@H:7]([C@@H:9]1[C@@H:12]([C@H:13]([C:15]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[S:16])[CH3:14])[NH:11][C:10]1=[O:24])[CH3:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:34](=[O:41])[C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[O:36]>ClCCl>[CH2:38]([O:37][C:35](=[O:36])[C:34]([N:11]1[C@H:12]([C@H:13]([C:15]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[S:16])[CH3:14])[C@@H:9]([C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:26])[CH3:25])[CH3:8])[C:10]1=[O:24])=[O:41])[CH:39]=[CH2:40]

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 3018516Allyl chlorooxoacetate2 回HCID 22851409(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine

生成物 1

HCID 86747785(3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl] -4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine (5.12 g) in dichloromethane (50 ml) were added pyridine (1.8 ml) and allyl chloroglyoxylate (2.3 ml) successively at 0° C. After stirring for 2 hours at the same temperature, to the solution were added pyridine (0.9 ml) and allyl chloroglyoxylate (0.75 ml). After stirring for 1 hour at 0° C., the solution was washed with water, 1N hydrochloric acid and brine, and dried. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane=1:9) to afford (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine (4.77 g).

後処理

  1. stirringAfter stirring for 1 hour at 0° C.
  2. washthe solution was washed with water, 1N hydrochloric acid and brine
  3. customdried
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (ethyl acetate:hexane=1:9)

出典と根拠

ORDレコード
ord-b72e9caed46d4b28a0d016e8c4139a1e
出典データセット
uspto-grants-1994_04
特許番号
US05306816

反応ノート

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