Dicyclohexylcarbodiimide → 4-methyl-2-oxo-N-(2-oxo-2-phenylethyl)pentanamide

HRID 1535085ノート

反応式

HRID 1535085 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][CH:17]([CH3:24])[CH2:18][C:19](=[O:23])[C:20]([O-:22])=O.[Na+].Cl.[NH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH3:24][CH:17]([CH3:16])[CH2:18][C:19](=[O:23])[C:20]([NH:27][CH2:28][C:29](=[O:30])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:22]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 4137900Sodium 4-methyl-2-oxovalerate

生成物 1

HCID 148955584-methyl-2-oxo-N-(2-oxo-2-phenylethyl)pentanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of dicyclohexylcarbodiimide (DCC) (157 g) in dichloromethane (200 ml) was added dropwise over 2 hours to an efficiently stirred mixture of powdered sodium 4-methyl-2-oxopentanoate (115.5 g), 2-aminoacetophenone hydrochloride (130.4 g) and HOBT (103 g) in dichloromethane (1 liter). The mixture was stirred overnight and the insoluble dicyclohexylurea removed by filtration. The filtrate was concentrated and the residue redissolved in dichloromethane (500 ml). The mixture was filtered to remove a further quantity of dicyclohexylurea, and the filtrate was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml) and saturated sodium chloride solution (500 ml). The organic phase was dried and concentrated to give 4-methyl-2-oxo-N-(2-oxo-2-phenylethyl)pentanamide (C), as a foam (183.6 g), which was used without further purification; NMR (CDCl3) : 1.0 (d, 6H), 2.2 (m, 1H), 2.8 (d, 2H), 4.75 (d, 2H), 7.4-7.7 (m, 3H), 7.9 (br, 1H), 8.0 (m, 2H).

後処理

  1. customthe insoluble dicyclohexylurea removed by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue redissolved in dichloromethane (500 ml)
  4. filtrationThe mixture was filtered
  5. customto remove a further quantity of dicyclohexylurea
  6. washthe filtrate was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml) and saturated sodium chloride solution (500 ml)
  7. customThe organic phase was dried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e843ef30dbe248978321e619f17a5b73
出典データセット
uspto-grants-1992_02
特許番号
US05091425

反応ノート

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