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

HRID 539987

反応式

HRID 539987 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e23414674814296af705f34c43a7805
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

関連ノート

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