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

HRID 1173640

反応式

HRID 1173640 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-8cc9315d98d2401abba8f1195f84e21b
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

関連ノート

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