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

HRID 227565

반응식

HRID 227565 반응식
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].CO[C:18](OC)([CH3:20])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][O:6][C:18]([CH3:20])([CH3:19])[N:7]1[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])=[O:15]

참가 물질

5

반응물 3

HCID 64952,2-DimethoxypropaneHCID 495564Methyl N-(tert-butoxycarbonyl)serinateHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 51384973-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (34) in CH2Cl2, stirring under nitrogen at 0° C., was added 2,2-dimethoxypropane (29.5 mL, 237.9 mmol) and p-toluene sulfonic acid monohydrate (9.050 g, 47.58 mmol). The mixture was removed from the ice bath after 15 minutes and stirred at room temperature for 1.5 hours. The reaction mixture was poured into 50 mL of saturated NaHCO3 (aq) and extracted with diethyl ether (3×50). The organic layer was extracted with NaHCO3 and brine, then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on SiO2 (1:1 EtOAc/Hexanes) to yield 7.659 g (62%, 3 steps) of a clear liquid.

후처리

  1. customThe mixture was removed from the ice bath after 15 minutes
  2. additionThe reaction mixture was poured into 50 mL of saturated NaHCO3 (aq)
  3. extractionextracted with diethyl ether (3×50)
  4. extractionThe organic layer was extracted with NaHCO3 and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on SiO2 (1:1 EtOAc/Hexanes)
  9. customto yield 7.659 g (62%, 3 steps) of a clear liquid

출처 및 근거

ORD 기록
ord-f4e26cbfd17f43a99a07407087df0fdf
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560477B2

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