2,2-Dimethoxypropane → HCID 86639851, compound

HRID 2426973Notes

Reaction equation

HRID 2426973 reaction equation
[OH:1][C@@:2]([CH3:11])([CH2:9][OH:10])[C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4].CO[C:14](OC)([CH3:16])[CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:8][O:7][N:5]([CH3:6])[C:3]([C@:2]1([CH3:11])[CH2:9][O:10][C:14]([CH3:16])([CH3:15])[O:1]1)=[O:4]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 11480618(2S)-2,3-Dihydroxy-N-methoxy-2,N-dimethyl-propionamide

Product 1

HCID 86639851HCID 86639851, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound prepared in Example 130(a) (12.4 g), acetone (150 mL), acetone dimethylacetal (18 mL) and p-toluenesulfonic acid monohydrate (290 mg) were stirred at room temperature for an hour. The reaction mixture was concentrated, poured into a cold aqueous solution of sodium hydrogen carbonate and extracted with a mixed solution of ethyl acetate-hexane (1:1). The obtained organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuum condition and dried to give the title compound (8.4 g) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into a cold aqueous solution of sodium hydrogen carbonate
  3. extractionextracted with a mixed solution of ethyl acetate-hexane (1:1)
  4. washThe obtained organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuum condition
  7. customdried

Sources & evidence

ORD record
ord-7d9442ce4d7144f2ad036ee9c9bf288e
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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