Tris(furan-2-yl)phosphane → HCID 131717298, compound

HRID 1681158Notes

Reaction equation

HRID 1681158 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13](OS(C(F)(F)F)(=O)=O)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:42][CH:43]([O:45][C:46]1[C:49](=[O:50])[C:48](=[O:51])[C:47]=1[Sn](CCCC)(CCCC)CCCC)[CH3:44].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1CCCC1=O.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13]([C:47]3[C:48](=[O:51])[C:49](=[O:50])[C:46]=3[O:45][CH:43]([CH3:44])[CH3:42])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dioneHCID 88467567HCID 88467567, compound

Product 1

HCID 131717298HCID 131717298, compoundYield 75.4%

Reagents, catalysts & solvents 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of diphenylmethyl 7-(t-butyloxycarbonylamino)-3-trifluoromethylsulfonyloxy-3-cephem-4-carboxylate (307 mg, 0.50 mmol) and 4-(2-propoxy)-3-(tri-n-butylstannyl)cyclobut-3-ene-1,2-dione (236 mg, 0.55 mmol) in N-methyl-2-pyrrolidinone (NMP, 4.5 mL) was degassed with a gentle stream of argon. Tris(2-furyl)phosphine (11.5 mg, 0.050 mmol), zinc chloride (136 mg, 1.0 mmol), and bis(dibenzylideneacetone) palladium (0) (14.4 mg, 0.025 mmol) were successively added. The mixture was stirred at an oil bath temperature of 60°-65° C. for 0.5 hr and was diluted with ethyl acetate. The resulting solution was sequentially washed with saturated aqueous NH4Cl (3X), H2O, and saturated NaCl and then was dried over Na2SO4. The filtrate was concentrated, and a solution of the residue in acetonitrile was washed with n-pentane (3X). Removal of the acetonitrile left a dark oil which was chromatographed on SiO2 (19 g) with methylene chloride-acetone (97:3) to afford the title compound (228 mg, 75% yield) as a bright yellow solid. Recrystallization from diisopropyl ether gave the analytical sample.

Workup

  1. washThe resulting solution was sequentially washed with saturated aqueous NH4Cl (3X), H2O, and saturated NaCl
  2. dry with materialwas dried over Na2SO4
  3. concentrationThe filtrate was concentrated
  4. washa solution of the residue in acetonitrile was washed with n-pentane (3X)
  5. customRemoval of the acetonitrile
  6. waitleft a dark oil which
  7. customwas chromatographed on SiO2 (19 g) with methylene chloride-acetone (97:3)

Sources & evidence

ORD record
ord-08a66c05628142ab96203694a6701f7c
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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