Water → Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylate

HRID 373351

반응식

HRID 373351 반응식
[C:1]([O:5][C:6]([CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:12](SC3N(C)N=NN=3)[CH2:13][S:14][C@H:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:45]=CC=C[CH:41]=1.C(/[Sn](CCCC)(CCCC)CCCC)=C/C.O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[C:1]([O:5][C:6]([CH:8]1[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:23])=[C:12](/[CH:41]=[CH:40]\[CH3:45])[CH2:13][S:14][C@H:9]12)=[O:7])([CH3:3])([CH3:4])[CH3:2]

참가 물질

9

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 10914524(Z)-Tri-n-butyl(1-propenyl)tinHCID 67918291Diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate

생성물 1

HCID 131717638Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylate수율 139.8%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate (IId, 0.125 g, 0.000215 mole), bis(dibenzylideneacetone)palladium (0.0062 g, 0.00001075 mole), triphenyl phosphine (0.0084 g, 0.000032 mole), zinc chloride (0.0586 g, 0.00043 mole) and Z-1-propenyltributyl stannane (0.071 g, 0.000215 mole) in dry tetrahydrofuran (2 mL) was refluxed under argon atmosphere for 20 h. After no further conversion of starting compound IId took place, water and ethyl acetate were added. The organic phase was separated, dried and concentrated. The crude product dissolved in acetonitrile and the acetonitrile solution was washed three times with equal volumes of pentane. Flash chromatography with 20% ethyl acetate in hexane gave the title product (0.022 g, 20%) as a foam. Also recovered was 0.0435g (34.8%) of starting compound IId.

후처리

  1. temperaturewas refluxed under argon atmosphere for 20 h
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe crude product dissolved in acetonitrile
  6. washthe acetonitrile solution was washed three times with equal volumes of pentane

출처 및 근거

ORD 기록
ord-5aea3cdc63fc46858d5c54d168ca7d17
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162521

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