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

HRID 444675노트

반응식

HRID 444675 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da54b4a98396482e887b5790f7362497
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476043B2

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