Dicyclohexylcarbodiimide → 2,5-Dimethylcyclopentyl N-t-butoxycarbonyl-1-aminocyclopropanecarboxylate

HRID 2232692ノート

反応式

HRID 2232692 の反応式
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH3:7])[CH:3]1[OH:8].[C:9]([O:13][C:14]([NH:16][C:17]1([C:20](O)=[O:21])[CH2:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:9]([O:13][C:14]([NH:16][C:17]1([C:20]([O:8][CH:3]2[CH:4]([CH3:7])[CH2:5][CH2:6][CH:2]2[CH3:1])=[O:21])[CH2:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 133801502,5-Dimethylcyclopentan-1-ol

生成物 1

HCID 212439622,5-Dimethylcyclopentyl N-t-butoxycarbonyl-1-aminocyclopropanecarboxylate

試薬・触媒・溶媒 2

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

実験手順

To a solution of 2,5-dimethylcyclopentanol (0.55 g), compound 1 (0.97 g), and 4-(dimethylamino)pyridine (0.06 g.) in methylene chloride (100 ml) was added dicyclohexylcarbodiimide (1.09 g.), and the resulting mixture was stirred overnight. The precipitated dicyclohexylurea was removed by filtration, and the filtrate was evaporated. Ethyl acetate was then added to the residue, and the mixture was filtered again. The filtrate was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate, and water, dried over magnesium sulfate, and the solvent was evaporated to a colorless oil (1.18 g. 83%). The product was purified by column chromatography on silica gel, 4:1 hexane:ethyl acetate, eluent.

後処理

  1. customThe precipitated dicyclohexylurea was removed by filtration
  2. customthe filtrate was evaporated
  3. additionEthyl acetate was then added to the residue
  4. filtrationthe mixture was filtered again
  5. washThe filtrate was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate, and water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated to a colorless oil (1.18 g. 83%)
  8. customThe product was purified by column chromatography on silica gel, 4:1 hexane

出典と根拠

ORDレコード
ord-ba7a58116e30486790ae07009ec089d7
出典データセット
uspto-grants-1988_11
特許番号
US04788332

反応ノート

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