Citric Acid → tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate

HRID 1173640

반응식

HRID 1173640 반응식
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([CH2:11][OH:12])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([CH:11]=[O:12])[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 8471TriethylamineHCID 11263954tert-butyl N-[(2S)-1-hydroxybutan-2-yl]carbamate

생성물 1

HCID 10241556tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate수율 85%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

A solution of tert-butyl[(1S)-1-(hydroxymethyl)propyl]carbamate (30.0 g) in dimethyl sulfoxide (300 mL) was ice-cooled under a nitrogen atmosphere, and triethylamine (64.4 mL) and a solution of sulfur trioxide•pyridine complex (80.7 g) in dimethyl sulfoxide (300 mL) were successively added. The mixture was stirred at the same temperature for 30 min and then at room temperature for 3 hr, 1 mol/L aqueous citric acid solution (500 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%) to give the title compound as a white powder (yield: 24.3 g, 85%).

후처리

  1. temperaturecooled under a nitrogen atmosphere
  2. waitat room temperature for 3 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe obtained organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%)

출처 및 근거

ORD 기록
ord-8cc9315d98d2401abba8f1195f84e21b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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