Methyl iodide → 4-(3-Adamantan-1-yl-ureido)butyric Acid Methyl Ester

HRID 444675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444675
[C:1]12([NH:11][C:12](=[O:20])[NH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:21]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:21][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12]([NH:11][C:1]12[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2)=[O:20]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 114259954-(3-Adamantan-1-yl-ureido)butyric acid

Produkt 1

HCID 114378554-(3-Adamantan-1-yl-ureido)butyric Acid Methyl EsterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (0.15 g, 0.54 mmol), K2CO3 (0.09 g, 0.64 mmol), and iodomethane (0.04 mL, 0.59 mmol) in DMF (20 mL) was stirred at room temperature for 20 h. Then the product was extracted with ether (20 mL), and the ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL), dried over Na2SO4, and evaporated to afford 0.15 g (95%) of 883: 1H NMR (CDCl3) 1.66-1.68 (6H, m), 1.81 (2H, quint, J=6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.37 (2H, t, J=6.9 Hz), 3.16 (2H, q, J=6.9 Hz), 3.68 (3H, s), 4.09 (1H, s), 4.25 (1H, s); LC-MS (ESI) m/z calcd for C16H26N2O3 [M+H]+ 295.19. found [M+H]+ 295.24; mp 114 C. Anal. (C16H26N2O3) C, H, N.

Aufarbeitung

  1. extractionThen the product was extracted with ether (20 mL)
  2. washthe ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-da54b4a98396482e887b5790f7362497
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476043B2

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