Methanol → Methyl 6-(benzyloxycarbonylamino)hexanoate

HRID 1936606

Reaction equation

HRID 1936606 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 43404641Methyl 6-(benzyloxycarbonylamino)hexanoateYield 58%

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a44e1eee59e044ffbff05a94dac46684
Source dataset
uspto-grants-2002_05
Patent number
US06391877B1

Linked notes

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