Methanol → Methyl 6-(benzyloxycarbonylamino)hexanoate

HRID 1936606

반응식

HRID 1936606 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:24]O>>[CH3:24][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

생성물 1

HCID 43404641Methyl 6-(benzyloxycarbonylamino)hexanoate수율 58%

실험 절차

To a solution of 6-benzyloxycarbonylamino-hexanoic acid (10 g, 38 mmol) in methanol (200 mL) at room temperature was added thionyl chloride (11 g, 95 mmol). The reaction mixture was then refluxed for 16 h. The solvent was concentrated in vacuo, the residue was dissolved in ethyl acetate (200 mL) and washed with brine (3×150 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (silica, 14% ethyl acetate in hexane) to afford the titled compound (6.2 g, 58%), a colorless liquid.

후처리

  1. temperatureThe reaction mixture was then refluxed for 16 h
  2. concentrationThe solvent was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with brine (3×150 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (silica, 14% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-a44e1eee59e044ffbff05a94dac46684
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391877B1

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