Methanol → Methyl 6-(benzyloxycarbonylamino)hexanoate

HRID 1581958

Reaktionsgleichung

Reaktionsgleichung von HRID 1581958
[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]

Komponenten

4

Edukt 3

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

Produkt 1

HCID 43404641Methyl 6-(benzyloxycarbonylamino)hexanoateAusbeute 58 %

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fa5b3bb131d64f7387810ee0ca0cb147
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734182B2

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