Acetic Acid → HCID 10178734, compound

HRID 985383Notes

Reaction equation

HRID 985383 reaction equation
C(O)(=O)C.[Si]([O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH:20]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:21][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:15][C:14]=1[O:37][CH3:38])(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH:20]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:21][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:15][C:14]=1[O:37][CH3:38]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 22506583HCID 22506583, compound

Product 1

HCID 10178734HCID 10178734, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Glacial acetic acid (130 ml) was added to 500 ml of a THF solution containing a mixture of diethyl β-(4-t-butyldimethylsilyloxy-3-methoxy-5-methylphenyl)-β-[N-(3-pyridyl)-amino]-ethylphosphonate (90.5 g, 0.18 mol) and tetrabutylammonium fluoride trihydrate (TBAF) (224.5 g, 0.71 mol). After stirring at 20° C. for 3 h a GLC test showed that the Tbs protected compound has entirely reacted. The reaction mixture was extracted with dichloromethane, the organic phase was washed with a saturated bicarbonate solution, dried over MgSO4 and evaporated. Purification by column chromatography (silica gel, 9/1 CH2Cl2/MeOH) gave 53 g of pure fractions. Recrystallization from a mixture of petroleum ether/CH2Cl2 gave 27 g (39%) of the title compound as a white solid, mp=156-158° C.

Workup

  1. additioncontaining
  2. customhas entirely reacted
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. washthe organic phase was washed with a saturated bicarbonate solution
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification by column chromatography (silica gel, 9/1 CH2Cl2/MeOH)
  8. customgave 53 g of pure fractions
  9. customRecrystallization
  10. additionfrom a mixture of petroleum ether/CH2Cl2

Sources & evidence

ORD record
ord-8a2f0313759a4af9903d3bed55d488b3
Source dataset
uspto-grants-2005_03
Patent number
US06872711B2

Reaction notes

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