2,2-Dimethoxypropane → HCID 67157484, compound

HRID 901800Notes

Reaction equation

HRID 901800 reaction equation
C([O:9][C@@H:10]1[C@@H:17]2[C@@H:13]([N:14]([CH:18]([CH2:21][OH:22])[CH2:19][OH:20])[O:15][CH2:16]2)[C@H:12]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:11]1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C1C=CC=CC=1.CO[C:41](OC)([CH3:43])[CH3:42].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+].C[O-].[Na+].[Cl-].[NH4+]>CC(C)=O>[CH2:32]([O:31][C@@H:11]1[C@@H:12]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:13]2[N:14]([CH:18]3[CH2:21][O:22][C:41]([CH3:43])([CH3:42])[O:20][CH2:19]3)[O:15][CH2:16][C@@H:17]2[C@H:10]1[OH:9])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 6

HCID 64952,2-DimethoxypropaneHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10942334Sodium MethoxideHCID 67157332HCID 67157332, compound

Product 1

HCID 67157484HCID 67157484, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound (1.20 g, 2.31 mmol) synthesized in Example 16 (16a) was dissolved in acetone (30 mL) and 2,2-dimethoxy propane (2.27 mL, 18.5 mmol) and p-toluenesulfonic acid monohydrate (660 mg, 3.47 mmol) were added thereto, followed by stirring of the mixture at room temperature for 15 minutes. After saturated aqueous sodium hydrogencarbonate (50 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with ethyl acetate (50 mL), the organic layer was washed with saturated brine (50 mL). The solvent was distilled off under reduced pressure and the residue was dissolved in methanol. Sodium methoxide (0.4 mL, 1.96 mmol) was added thereto and the mixture was stirred at room temperature for 20 minutes. After saturated aqueous ammonium chloride (50 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with ethyl acetate (50 mL), the organic layer was washed with saturated brine (50 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1, V/V) to obtain the desired title compound (840 mg, yield 80%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washthe organic layer was washed with saturated brine (50 mL)
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in methanol
  5. stirringthe mixture was stirred at room temperature for 20 minutes
  6. extractionthe mixture was extracted with ethyl acetate (50 mL)
  7. washthe organic layer was washed with saturated brine (50 mL)
  8. dry with materialdried with anhydrous sodium sulfate
  9. distillationby distilling off of the solvent under reduced pressure
  10. customThe residue was purified

Sources & evidence

ORD record
ord-5f437520eaf04e46aa211b654f55d257
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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