Tributylvinyltin → Diphenylmethyl 7-Phenoxyacetamido-3-vinyl-3-cephem-4-carboxylate

HRID 5545

反応式

HRID 5545 の反応式
[CH:1]([Sn](CCCC)(CCCC)CCCC)=[CH2:2].[O:16]([CH2:23][C:24]([NH:26][CH:27]1[C:55](=[O:56])[N:29]2[C:30]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:31](OS(F)(=O)=O)[CH2:32][S:33][C@H:28]12)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN1CCCC1=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:16]([CH2:23][C:24]([NH:26][CH:27]1[C:55](=[O:56])[N:29]2[C:30]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:31]([CH:1]=[CH2:2])[CH2:32][S:33][C@H:28]12)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

6

反応物 2

HCID 81998TributylvinyltinHCID 88424184Diphenylmethyl 7-Phenoxyacetamido-3-[(fluorosulfonyl)oxy]-3-cephem-4-carboxylate

生成物 1

HCID 14608937Diphenylmethyl 7-Phenoxyacetamido-3-vinyl-3-cephem-4-carboxylate収率 88.8%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of palladium (II) acetate (3.6 mg, 0.016 mmol, 0.1 eq.) in 1-methyl-2-pyrrolidinone (2 mL) was treated with vinyl tri-n-butylstannane (58.4 mL, 0.2 mmol, 1.2 eq.) under an inert atmosphere and allowed to stir for 3 minutes. The resulting dark suspension was then treated with diphenylmethyl 7-phenoxyacetamido-3-[(fluorosulfonyl) oxy]-3-cephem-4-carboxylate (100.0 mg, 0.16 mmol, 1.0 eq.) in one portion and the reaction mixture was allowed to stir for 10 minutes. The reaction mixture was diluted with ethyl acetate and washed with 3×20 mL of water. The organic fraction was dried over magnesium sulfate then concentrated. The crude brown residue was purified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL) to remove the residual stannane and then with 10% ethyl acetate in dichloromethane (75 mL), which upon concentration furnished 74.8 mg (85%) of the title compound as a white solid.

後処理

  1. stirringto stir for 10 minutes
  2. washwashed with 3×20 mL of water
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. concentrationthen concentrated
  5. filtrationThe crude brown residue was purified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL)
  6. customto remove the residual stannane
  7. concentrationwith 10% ethyl acetate in dichloromethane (75 mL), which upon concentration

出典と根拠

ORDレコード
ord-e1035b9ffe964abea5e21dc8c9fb7b3c
出典データセット
uspto-grants-1993_09
特許番号
US05245027

関連ノート

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