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

HRID 373351

Reaktionsgleichung

Reaktionsgleichung von HRID 373351
[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]

Komponenten

9

Edukt 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

Produkt 1

HCID 131717638Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylateAusbeute 139,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5aea3cdc63fc46858d5c54d168ca7d17
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162521

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