2-Methyl-2-butene → (3S,4S)-4-(1-carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1196200ノート

反応式

HRID 1196200 の反応式
[CH:1]([C:3]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4])=[O:2].CC(=CC)C.Cl([O-])=[O:48].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C(O)(C)(C)C>[C:1]([C:3]([C@H:5]1[N:8]([CH:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4])([OH:48])=[O:2]

参加物

6

反応物 4

HCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 23668197Sodium ChloriteHCID 86745328HCID 86745328、化合物

生成物 1

HCID 67919435(3S,4S)-4-(1-carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

(3S,4S)-4-(1-Formylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (4.5 g) was dissolved in t-butanol (380 ml). After addition of 2-methyl-2-butene (42.5 ml) thereto, there was dropwise added an aqueous solution (72.3 ml) of sodium chlorite (7.15 g) and disodium hydrogenphosphate (7.15 g). The resulting mixture was stirred at room temperature for 1 hour and concentrated in vacuo at 40° C. or lower. The concentrate was diluted with ethyl acetate (150 ml) and water (75 ml), and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (80 ml), and the combined ethyl acetate layer was washed with brine (150 ml) and extracted with a saturated sodium bicarbonate solution (150 ml). The alkaline layer was acidified with conc. hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extracts were washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone.

後処理

  1. concentrationconcentrated in vacuo at 40° C.
  2. additionThe concentrate was diluted with ethyl acetate (150 ml) and water (75 ml)
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (80 ml)
  5. washthe combined ethyl acetate layer was washed with brine (150 ml)
  6. extractionextracted with a saturated sodium bicarbonate solution (150 ml)
  7. temperaturecooling
  8. extractionextracted with ethyl acetate
  9. washThe extracts were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationFiltration and concentration of the filtrate in vacuo

出典と根拠

ORDレコード
ord-5624eb492439470f8d733153526f295d
出典データセット
uspto-grants-1992_05
特許番号
US05112966

反応ノート

読み込み中…