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

HRID 620689노트

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HRID 620689 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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 chromotography on silica gel, 4:1 hexane:ethyl acetate, eluent. NMR (CDCl3): δ0.92 (t, 6H, 2CH3), 1.05-2.10 (m, 10H, cyclopentyl, cyclopropyl), 1.40 (s, 9H, t-Bu), 4.60 (dd., 1H, CO2CH), 5.05 (br. s, 1H, NH).

후처리

  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 chromotography on silica gel, 4:1 hexane

출처 및 근거

ORD 기록
ord-7feec6ad76db41efb9be6f67ada89f96
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822635

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