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

HRID 419758

반응식

HRID 419758 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ecb94918a35e424aba8e681fc8c7aea2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093395B2

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