2,2-Dimethoxypropane → (6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane

HRID 1196204ノート

反応式

HRID 1196204 の反応式
[OH:1][CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4].CO[C:25](OC)([CH3:27])[CH3:26].B(F)(F)F.CCOCC>ClCCl>[O:9]=[C:7]1[N:8]2[C@H:5]([C:3](=[CH2:4])[CH2:2][O:1][C:25]2([CH3:27])[CH3:26])[C@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH3:11]

参加物

5

反応物 3

HCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 15000240(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

生成物 1

HCID 22843873(6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (3.7 g) and 2,2-dimethoxypropane (1.45 g) in dry dichloromethane (26 ml) was treated with boron trifluoride-etherate (0.14 ml) at room temperature for 1.5 hours. The reaction mixture was washed successively with saturated sodium bicarbonate (15 and water (20 ml×2), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was purified by silica gel chromatography to yield (6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane.

後処理

  1. washThe reaction mixture was washed successively with saturated sodium bicarbonate (15 and water (20 ml×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo
  4. customgave an oily residue, which
  5. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-77f765386da447f8b8048fd551aa2463
出典データセット
uspto-grants-1992_05
特許番号
US05112966

反応ノート

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