Cyclopentane, methylene- → N-CBZ-O-(1-methylcyclopentyl)-L-serine methylester

HRID 653387

反応式

HRID 653387 の反応式
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][OH:17])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH2:19]=[C:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])O.[Na+]>ClCCl.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][O:17][C:20]1([CH3:19])[CH2:24][CH2:23][CH2:22][CH2:21]1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

参加物

6

反応物 3

HCID 73714Cyclopentane, methylene-HCID 516892Sodium BicarbonateHCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

生成物 1

HCID 15594942N-CBZ-O-(1-methylcyclopentyl)-L-serine methylester収率 78%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 6344Dichloromethane溶媒

実験手順

N-CBZ-L-serine methyl ester (3.15 g) was dissolved in 40 ml of dichloromethane at 0° C. under argon. Methylenecyclopentane (20 ml) was added, followed by 16 drops of concentrated sulfuric acid. The contents of the vessel were stirred at room temperature overnight then poured into dilute aqueous sodium hydrogen carbonate and extracted with chlorofrom (2×30 ml). The organic layer was dried over sodium sulfate and evaporated. The residual oil was chromatographed on silica gel with 50/50 petroleum ether/diethyl ether to give an oil (78% yield). The product, N-CBZ-O-(1-methylycyclopentyl)-L-serine methyl ester, was confirmed by NMR spectroscopy.

後処理

  1. extractionextracted with chlorofrom (2×30 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customThe residual oil was chromatographed on silica gel with 50/50 petroleum ether/diethyl ether

出典と根拠

ORDレコード
ord-6f5f8e0ae3f944828dc03e7b61083fa2
出典データセット
uspto-grants-1987_06
特許番号
US04676989

関連ノート

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