Dicyclohexylcarbodiimide → (RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrate

HRID 34599

反応式

HRID 34599 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]([C:20]1[N:25]=[CH:24][C:23]([CH:26]([CH:30]([CH3:32])[CH3:31])[C:27]([OH:29])=[O:28])=[CH:22][N:21]=1)([CH3:19])[CH3:18].[C:33]([CH:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=1)#[CH:34]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:19][C:17]([C:20]1[N:21]=[CH:22][C:23]([CH:26]([CH:30]([CH3:32])[CH3:31])[C:27]([O:29][CH:35]([C:33]#[CH:34])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:37]=2)=[O:28])=[CH:24][N:25]=1)([CH3:16])[CH3:18]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 129190923-Phenoxy-alpha-ethynylbenzylalcoholHCID 13911492(RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyric acid

生成物 1

HCID 13911493(RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrate収率 90.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of N,N'-dicyclohexylcarbodiimide (0.2 g) in dichloromethane (5 cm3) was added to a stirred mixture of (RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyric acid (0.26 g), (RS)-α-ethynyl-3-phenoxybenzyl alcohol (0.224 g), 4-dimethylaminopyridine (0.02 g) and dry dichloromethane (5 cm3) and the resultant mixture stirred for 2 hours. The precipitate which formed was removed by filtration and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residual oil was purified by column chromatography using a silica column eluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60° to 80° C., 1 part by volume) to yield (RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrate (0.4g), as a mixture of diastereoisomers.

後処理

  1. customThe precipitate which formed
  2. customwas removed by filtration
  3. concentrationthe filtrate concentrated by evaporation of the solvent under reduced pressure
  4. customThe residual oil was purified by column chromatography
  5. washeluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60° to 80° C., 1 part by volume)

出典と根拠

ORDレコード
ord-c386507b28164d92ae62632ecf157c70
出典データセット
uspto-grants-1988_08
特許番号
US04762835

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