1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → 2,5-Dimethylcyclopentyl N-t-butoxycarbonyl-1-aminocyclopropanecarboxylate

HRID 35444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35444
[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]>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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 dicyclohexylacarbodiimide (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 aqeuous 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.

Aufarbeitung

  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 aqeuous 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

Quellen und Nachweise

ORD-Eintrag
ord-c25432ba33814242995d179d36701e13
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766246

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