p-Toluenesulfonic acid monohydrate → HCID 86639851, compound

HRID 534137Notes

Reaction equation

HRID 534137 reaction equation
[OH:1][C@@:2]([CH3:11])([CH2:9][OH:10])[C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4].O.[CH3:13][C:14]1C=CC(S(O)(=O)=O)=C[CH:15]=1>COC(OC)(C)C>[CH3:8][O:7][N:5]([CH3:6])[C:3]([C@:2]1([CH3:11])[CH2:9][O:10][C:14]([CH3:15])([CH3:13])[O:1]1)=[O:4]

Participants

4

Reactant 2

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

Product 1

HCID 86639851HCID 86639851, compoundYield 581.6%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

(S)-2,3-dihydroxy-N-methoxy-N,2-dimethylpropanamide (32 g, 196 mmol) was dissolved in 2,2-dimethoxypropane (241 ml, 1961 mmol, 4-methylbenzenesulfonic acid hydrate (3.73 g, 19.6 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate, extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica plug (1.5 L, eluting with 25% EtOAc in hexanes) to afford (S)-N-methoxy-N,2,2,4-tetramethyl-1,3-dioxolane-4-carboxamide (23.1 g, 114 mmol, 58.0% yield).

Workup

  1. additionwas added
  2. customThe reaction was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica plug (1.5 L, eluting with 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-db58d6ef68534d9c80a663dd850f2292
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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