Tetrahydrofuran → HCID 59639654, compound

HRID 2249825Notes

Reaction equation

HRID 2249825 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[CH3:18])[C:8]([CH:19]=O)=[C:7]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:6]=1.C1C[O:31][CH2:30][CH2:29]1>C(OCC)C>[CH:22]1([N:21]2[C:7]3[N:6]=[C:5]([S:4][CH3:3])[N:10]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=4[CH3:18])[C:8]=3[CH:19]=[CH:29][C:30]2=[O:31])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 59639519HCID 59639519, compound

Product 1

HCID 59639654HCID 59639654, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylphosphonoacetate (3.87 mL, 0.01953 mol) in dry THF (56 mL) was treated with NaH (60% in mineral oil) (967.5 mg, 0.0243 mol). The mixture was stirred for 30 min giving a clear solution. The title compound from Example 180 (4.5 g, 0.0125 mol) in dry THF (75 mL) was added in one portion and the solution gently refluxed for 72 h. After cooling to 23°, the reaction mixture was diluted with ethyl ether, then washed in turn with satd aq NH4Cl and H2O. Organic layer was dried (Na2SO4), then evaporated to a viscous syrup which was flash chromatographed in methylene chloride-hexane gradient (20% to 0% hexane) to afford first 920 mg (19%) of the title compound as a white solid. LC MS (m/e)=384 (MH+). Rt=2.79 min.

Workup

  1. customgiving a clear solution
  2. temperaturethe solution gently refluxed for 72 h
  3. temperatureAfter cooling to 23°
  4. washwashed in turn with satd aq NH4Cl and H2O
  5. dry with materialOrganic layer was dried (Na2SO4)
  6. customevaporated to a viscous syrup which
  7. customchromatographed in methylene chloride-hexane gradient (20% to 0% hexane)

Sources & evidence

ORD record
ord-30ca65ddabb14087bc239f56ab23e2e7
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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