Dicyclohexylcarbodiimide → 2,N-dimethoxy-2,N-dimethyl-propionamide

HRID 1677435ノート

反応式

HRID 1677435 の反応式
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:24][O:25][NH:26][CH3:27]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([N:26]([O:25][CH3:24])[CH3:27])=[O:6]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 14232N,O-DimethylhydroxylamineHCID 98554652-Methoxy-2-methylpropanoic acid

生成物 1

HCID 866466872,N-dimethoxy-2,N-dimethyl-propionamide収率 14.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-methoxy-2-methyl-propionic acid (1.0 g, 8.46 mmol) in anhydrous dichloromethane (10 ml) was slowly treated with DCC (1M in DCM, 10.16 ml, 10.16 mmol), O,N-Dimethyl-hydroxylamine (991 mg, 10.16 mmol), DMAP (103 mg, 0.843 mmol), and TEA (1.42 ml, 10.16 mmol). The reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was partitioned between DCM/1N HCl. The organic layers were collected, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography using 5-60% EtOAc in hexanes as eluant providing 200 mg (14.66%) of 2,N-dimethoxy-2,N-dimethyl-propionamide as a colorless oil.

後処理

  1. customThe reaction mixture was partitioned between DCM/1N HCl
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6b14b86409254ae69e61daaa24b2366a
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

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