2,2-Dimethoxypropane → Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2401280ノート

反応式

HRID 2401280 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:11][CH2:12][CH2:13][OH:14])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CO[C:18](OC)([CH3:20])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[OH:14][CH2:13][CH2:12][CH2:11][C@H:8]1[CH2:9][O:10][C:18]([CH3:20])([CH3:19])[N:7]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15]

参加物

6

反応物 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate

生成物 1

HCID 10879805Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of tert-butyl[(2S)-1,5-dihydroxypentan-2-yl]carbamate (9.45 g), 2,2-dimethoxypropane (48 mL) and p-toluenesulfonic acid monohydrate (0.41 g) in chloroform (100 mL) was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the solvent was distilled off under reduced pressure. Ethyl acetate was added thereto, and the resulting mixture was washed with water and brine, followed by drying over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-0:100) to afford tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.05 g).

後処理

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionEthyl acetate was added
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialby drying over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-0:100)

出典と根拠

ORDレコード
ord-8d217c071a8f4e69a9ecd38399467e77
出典データセット
uspto-grants-2014_08
特許番号
US08796272B2

反応ノート

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