Methanol → Methyl 6-(benzyloxycarbonylamino)hexanoate

HRID 322487

反応式

HRID 322487 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 43404641Methyl 6-(benzyloxycarbonylamino)hexanoate収率 58%

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e0d8b7b317c5403cb708f5a48d2b50a2
出典データセット
uspto-grants-2001_04
特許番号
US06211241B1

関連ノート

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