Methyl iodide → Methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

HRID 743457ノート

反応式

HRID 743457 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].N12CCCN=C1CCCC[CH2:15]2.CI>C1C=CC=CC=1>[CH3:15][O:12][C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:9]

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

生成物 1

HCID 14018930Methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate収率 86.4%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of N-t-butoxycarbonyl-sarcosine (50 g; 0.264 mol) in 700 ml of benzene was added 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU; 40.19 g, 0.264 mol) in one portion. To the above clear solution was added 74.84 g (0.528 mol) of methyl iodide in one portion and the resulting clear solution was allowed to reflux for 7 hours. After adding additional methyl iodide (16 ml), the reaction mixture was refluxed with stirring and then cooled to room temperature, and stirred overnight. The reaction mixture was filtered, the residue washed with ether, and the combined filtrate was washed with water, saturated sodium bicarbonate solution, and brine. The resulting organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 46.38 g (86.4 %) of N-t-butoxycarbonyl-sarcosine methyl ester as a yellow oil.

後処理

  1. temperatureto reflux for 7 hours
  2. temperaturethe reaction mixture was refluxed
  3. stirringstirred overnight
  4. filtrationThe reaction mixture was filtered
  5. washthe residue washed with ether
  6. washthe combined filtrate was washed with water, saturated sodium bicarbonate solution, and brine
  7. dry with materialThe resulting organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-dde8614e69a54880bcbec690a016cde2
出典データセット
uspto-grants-1996_09
特許番号
US05556909

反応ノート

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