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

HRID 227565

反応式

HRID 227565 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4e26cbfd17f43a99a07407087df0fdf
出典データセット
uspto-grants-2009_07
特許番号
US07560477B2

関連ノート

読み込み中…