2,2-Dimethoxypropane → 3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

HRID 539987

반응식

HRID 539987 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:18](OC)([CH3:20])[CH3:19]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:19][C:18]1([CH3:20])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][O:15]1

참가 물질

5

반응물 2

HCID 64952,2-DimethoxypropaneHCID 377723N-Boc-D-serine methyl ester

생성물 1

HCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate수율 63.6%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

A solution of methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate (22 g, 0.1 mol), 2,2-dimethoxypropane (20.8 g, 0.2 mol) and 4-methylbenzene-1-sulfonic acid (0.5 g) in toluene was heated with stirring at 110° C. overnight. The solvent was removed under reduced pressure. The residue was treated with ethyl acetate, washed with water and brine. The organic layer was dried over sodium sulfate, concentrated under reduced pressure. The residue distilled at 0.6 mbar to give 16.5 g of 3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate (yield was 63.6%) as an amber oil.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was treated with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue distilled at 0.6 mbar

출처 및 근거

ORD 기록
ord-8e23414674814296af705f34c43a7805
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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