Diethyl Ether → HCID 178477397、化合物

HRID 267488ノート

反応式

HRID 267488 の反応式
[F:1][C:2]([F:34])([F:33])[S:3]([CH2:5][C:6]([NH:8][CH:9]1[C:31](=[O:32])[N:11]2[C:12]([C:24]([O:26]C(C)(C)C)=[O:25])=[C:13]([CH:16]([S:18][C:19]3[NH:23][N:22]=[N:21][N:20]=3)[CH3:17])[CH2:14][S:15][C@H:10]12)=[O:7])=[O:4].CCOCC>FC(F)(F)C(O)=O>[F:34][C:2]([F:1])([F:33])[S:3]([CH2:5][C:6]([NH:8][CH:9]1[C:31](=[O:32])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH:16]([S:18][C:19]3[NH:23][N:22]=[N:21][N:20]=3)[CH3:17])[CH2:14][S:15][C@H:10]12)=[O:7])=[O:4]

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 178477377HCID 178477377、化合物

生成物 1

HCID 178477397HCID 178477397、化合物

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of 1.54 g (0.004 mol) of 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, t-butyl ester and 0.825 g (0.004 mol) of dicyclohexylcarbodiimide in 50 ml of benzene was added 0.704 g (0.004 mol) of trifluoromethylsulfinylacetic acid. The reaction mixture was stirred at 25° for 2 hr., then it was filtered and adsorbed onto 4 g of silica gel. Chromatography on 100 g of silica gel with 50:50 benzene-ethyl acetate gave 1.55 g (69 percent) of 7-trifluoromethylsulfinylacetamido-3-(1-methyl-1,2,3,4-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, t-butyl ester as a white foam. The ester was dissolved in 9 ml of trifluoroacetic acid and stirred at 25° for 5 minutes, then added dropwise to 200 ml of ether. The precipitate was collected, dissolved in 5 percent sodium bicarbonate and the solution was diluted to 150 ml. After extraction with ethyl acetate the aqueous phase was acidified to pH 1.5 and extracted thrice more with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated to 35 ml, to which residue (the free acid) was added a solution of 1.5 of 30 percent sodium 2-ethylhexanoate in isopropanol followed by 200 ml of ether. The precipitated salt was collected, reprecipitated from methanol-ether and dried in vacuo to give 0.680 g of product.

後処理

  1. customThe precipitate was collected
  2. dissolutiondissolved in 5 percent sodium bicarbonate
  3. additionthe solution was diluted to 150 ml
  4. extractionAfter extraction with ethyl acetate the aqueous phase
  5. extractionextracted thrice more with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated to 35 ml, to which residue (the free acid)
  8. additionwas added a solution of 1.5 of 30 percent sodium 2-ethylhexanoate in isopropanol
  9. customThe precipitated salt was collected
  10. customreprecipitated from methanol-ether
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-9d49d74a67154a6aa75cae2b9001006a
出典データセット
uspto-grants-1976_03
特許番号
US03943127

反応ノート

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