Hydrogen Peroxide → p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate-1,1-dioxide

HRID 258009

反応式

HRID 258009 の反応式
[NH2:1][C@@H:2]1[C:25](=[O:26])[N:4]2[C:5]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7]S[C@H:3]12.OO.[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+]>C(OCC)(=O)C.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH2:1][C@@H:2]1[C:25](=[O:26])[N:4]2[C:5]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:29](=[O:32])(=[O:30])[C@H:3]12

参加物

6

反応物 3

HCID 784Hydrogen Peroxide2 回HCID 24437Sodium SulfiteHCID 131718254p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate

生成物 1

HCID 131718253p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate-1,1-dioxide

試薬・触媒・溶媒 2

HCID 150191Sodium Tungstate Dihydrate触媒HCID 8857Ethyl Acetate溶媒

実験手順

p-Methoxybenzyl 7β-amino-3-azidomethyl-3-cephem-4-carboxylate (17.15 g, 0.046 mol) in ethyl acetate was cooled to 15° C., sodium tungstate dihydrate (1.52 g, 0.0046 mol) was added followed by hydrogen peroxide (30%, 20.73 ml) in one portion and the stirring was continued at room temperature. After two hours an additional portion of hydrogen peroxide (5.18 ml) was added and the reaction mixture was stirred at room temperature for a total period of 18 h; the mixture was cooled to 10° C. and a solution of sodium sulphite (10%, 600 ml) was added while stirring. Organic layer was separated out, washed with aq. sodium bicarbonate solution, brine and dried (Na2SO4). Evaporation of the solvent in vacuo gave a foam (12 g) which was purified over a silica column using hexane-ethyl acetate (1:3) as eluant to give the pure product as a white foam (6.8 g, 36.5%). IR (Nujol) ν max 2083 cm-1.

後処理

  1. customwas continued at room temperature
  2. temperaturethe mixture was cooled to 10° C.
  3. stirringwhile stirring
  4. customOrganic layer was separated out
  5. washwashed with aq. sodium bicarbonate solution, brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent in vacuo

出典と根拠

ORDレコード
ord-4181c31959a440168d9c37b195912fba
出典データセット
uspto-grants-1993_11
特許番号
US05264429

関連ノート

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