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

HRID 1736321노트

반응식

HRID 1736321 반응식
[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]

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-25d52389f85a44ebbeb4261fa8af7642
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541168

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