2,2-Dimethoxypropane → 3-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

HRID 419758

Reaction equation

HRID 419758 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13][OH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CO[C:18](OC)([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:19][C:18]1([CH3:20])[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH:4]([C:3]([O:2][CH3:1])=[O:15])[CH2:13][O:14]1

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 51384973-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylateYield 117.5%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 241BenzeneSolvent

Procedure

Commercially available N-tert-butoxycarbonyl-serine methyl ester (2.0 g, 9.122 mmol), 2,2-dimethoxypropane (1.9 g, 18.24 mmol), and pyridinium-p-toluene sulfonate (26 mg, 137 μmol) were dissolved in benzene (29 ml) and heated under reflux for 15 hours. A saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with diethylether; the organic layer was subsequently washed with a saturated sodium chloride solution. The washed product was then dried over anhydrous magnesium sulfate and filtered, and the filtrate was subsequently concentrated. The resulting concentrate was purified by silica gel column chromatography to produce 3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (2.78 g, 91% yield).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. extractionthe mixture was extracted with diethylether
  4. washthe organic layer was subsequently washed with a saturated sodium chloride solution
  5. dry with materialThe washed product was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was subsequently concentrated
  8. concentrationThe resulting concentrate
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecb94918a35e424aba8e681fc8c7aea2
Source dataset
uspto-grants-2012_01
Patent number
US08093395B2

Linked notes

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