Dicyclohexylcarbodiimide → 1-(4-methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester

HRID 262752ノート

反応式

HRID 262752 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]([CH3:11])[C:8]([OH:10])=O)=[O:4].[C:12]([O:16][C:17](=[O:23])[C@@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1)([CH3:15])([CH3:14])[CH3:13].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:12]([O:16][C:17](=[O:23])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:8](=[O:10])[CH:7]([CH3:11])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 131928974-Carbomethoxy-2-methylbutanoic acid

生成物 1

HCID 706097971-(4-methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Methoxycarbonyl-2-methylbutanoic acid (3.1 g.) and L-proline tert.-butyl ester (3.78 g.) are dissolved in dichloromethane (40 ml.). The solution is chilled with stirring in an ice bath and dicyclohexylcarbodiimide (4.12 g.) is added. After stirring 15 minutes in the ice bath and 18 hours at room temperature, the precipitate is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is chromatographed on a column of silica gel with chloroform to obtain 1-(4-methoxycarbonyl-2-methylbutanoyl)-L-proline tert.-butyl ester, yield 3.5 g.

後処理

  1. temperatureThe solution is chilled
  2. filtrationthe precipitate is filtered off
  3. concentrationthe filtrate is concentrated to dryness in vacuo
  4. customThe residue is chromatographed on a column of silica gel with chloroform

出典と根拠

ORDレコード
ord-518374b0def448efb29b0ae7f7eefceb
出典データセット
uspto-grants-1979_05
特許番号
US04154937

反応ノート

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