(Z)-Tri-n-butyl(1-propenyl)tin → Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylate

HRID 37350

반응식

HRID 37350 반응식
[CH:1](/[Sn](CCCC)(CCCC)CCCC)=[CH:2]/[CH3:3].[O:17]([CH2:24][C:25]([NH:27][CH:28]1[C:56](=[O:57])[N:30]2[C:31]([C:40]([O:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:32](OS(F)(=O)=O)[CH2:33][S:34][C@H:29]12)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:17]([CH2:24][C:25]([NH:27][CH:28]1[C:56](=[O:57])[N:30]2[C:31]([C:40]([O:42][CH:43]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:32](/[CH:1]=[CH:2]\[CH3:3])[CH2:33][S:34][C@H:29]12)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 2

HCID 10914524(Z)-Tri-n-butyl(1-propenyl)tinHCID 88424184Diphenylmethyl 7-Phenoxyacetamido-3-[(fluorosulfonyl)oxy]-3-cephem-4-carboxylate

생성물 1

HCID 14608940Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylate수율 92.9%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of palladium (II) acetate (3.6 mg, 0.016 mmole, 0.1 eq.) in dichloromethane (2 mL) was treated with Z-1-propenyl tri-n-butylstannane (66.2 mg, 0.2 mmole, 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 mmole, 1.0 eq.) in one portion and the reaction mixture was allowed to stir for 10 minutes. The reaction mixture was diluted with additional dichloromethane and washed with water (1×10 mL). The organic fraction was dried over magnesium sulfate and 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 (50 mL) which upon concentration furnished 80.4 mg (89%) of the title compound as a pale yellow solid. The product was then recrystallized from isopropyl alcohol to afford 62.3 mg (69%) of a white solid, mp. 103°-104° C.

후처리

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

출처 및 근거

ORD 기록
ord-512fd01efe9d4d2bbe59666e4c073c20
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420269

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