Water → HCID 14167864, compound

HRID 373350Notes

Reaction equation

HRID 373350 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30][CH:31]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:29])=[C:15](SC4SC5C=CC=CC=5N=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1C=C[CH:48]=[C:47]1P(C1OC=CC=1)C1OC=CC=1.C([Sn](CCCC)(CCCC)CCCC)=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]1([CH2:7][C:8]([NH:10][CH:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30][CH:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[O:29])=[C:15]([CH:47]=[CH2:48])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 962WaterHCID 81998TributylvinyltinHCID 521585Tris(furan-2-yl)phosphaneHCID 67688232HCID 67688232, compound

Product 1

HCID 14167864HCID 14167864, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
65 °C

Procedure

A mixture of diphenylmethyl 7-phenylacetamido-3-[(benzothiazol-2-yl)thio]-3-cephem-4-carboxylate (IIc, 0.0973 g, 0.00015 mole), bis(dibenzylidene acetone)palladium (0.0044 g, 0.00000765 mole), tri(2-furyl)phosphine (0.006 g, 0.000026 mole), zinc chloride (0.042 g, 0.003 mole) and vinyl tributyl stannane (0.055 mL, 0.00018 mole) in dry tetrahydrofuran (3 mL) was heated under argon atmosphere at 65° C. for 18 h. After that period HPLC indicated no further conversion of compound IIc. Water and ethyl acetate was added to the reaction mixture, and the two phases were separated. The organic phase was separated, dried and concentrated. The crude product obtained was dissolved in acetonitrile and the acetonitrile solution was washed three times with equal volumes of pentane. Flash chromatography (5% dichloromethane in ethyl acetate) recovered starting compound IIc (0.041 g, 42%) and afforded product IIIa (0.0133 g, 17%, 29% when corrected for recovered starting material) as a yellow foam. Recrystallization from ethanol gave the analytical sample.

Workup

  1. waitAfter that period HPLC indicated
  2. customthe two phases were separated
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-36dd2315a66e46919a917073e24e4b4e
Source dataset
uspto-grants-1992_11
Patent number
US05162521

Reaction notes

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