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

HRID 373351

Reaction equation

HRID 373351 reaction equation
[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]

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5aea3cdc63fc46858d5c54d168ca7d17
Source dataset
uspto-grants-1992_11
Patent number
US05162521

Linked notes

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