Bromomethyl pivalate → Pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

HRID 1153774ノート

反応式

HRID 1153774 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13](=[O:26])[N:8]2[C:9]=1[C:10]([O-:12])=[O:11].[Na+].[C:28]([O:34][CH2:35]Br)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:26])[N:8]2[C:9]=1[C:10]([O:12][CH2:35][O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:11]

参加物

5

反応物 2

HCID 15916453Bromomethyl pivalateHCID 67721394Sodium 3-methoxymethyl7-phenoxyacetamido-3-cephem-4-carboxylate

生成物 1

HCID 70432401Pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate収率 61%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1 g of sodium 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate was disssolved in 50 ml of dimethyl sulphoxide, and 975 mg of pivaloyloxymethyl bromide were added thereto, after which the mixture was stirred at room temperature for 15 minutes. The mixture was then diluted with 200 ml of ethyl acetate, washed in turn with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of potassium bisulphate, and then dried over anhydrous magnesium sulphate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure and the resulting residue was chromatographed through 100 g of silica gel eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to afford 750 mg of the desired pivaloyloxymethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate.

後処理

  1. washwashed in turn with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of potassium bisulphate
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationAfter filtering off the drying agent
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was chromatographed through 100 g of silica gel
  6. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-c7129909591d40bba2983db349907602
出典データセット
uspto-grants-1984_12
特許番号
US04486425

反応ノート

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