2,2-Dimethoxypropane → HCID 86644162, compound

HRID 1523686Notes

Reaction equation

HRID 1523686 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.CC1C=CC(S(O)(=O)=O)=CC=1>>[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

4

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 11228975HCID 11228975, compound

Product 1

HCID 86644162HCID 86644162, compoundYield 57.7%

Procedure

(R)-2,3-dihydroxy-N-methoxy-N,2-dimethylpropanamide (32 g, 196 mmol) was dissolved in 2,2-dimethoxypropane (241 ml, 1961 mmol) and 4-methylbenzenesulfonic acid hydrate (3.73 g, 19.6 mmol) was added and stirred at ambient temperature overnight. The reaction was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2, extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford (R)—N-methoxy-N,2,2,4-tetramethyl-1,3-dioxolane-4-carboxamide (22.9 g, 113 mmol, 57.5% yield).

Workup

  1. customThe reaction was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9383b66b3644725b17d731ace066895
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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