Gamma-Aminobutyric Acid → 4-(3-Adamantan-1-yl-ureido)butyric acid

HRID 1444640노트

반응식

HRID 1444640 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8]12([N:18]=[C:19]=[O:20])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.Cl.[CH3:22]N(C=O)C>>[CH3:22][O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][NH:1][C:19]([NH:18][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:20].[C:8]12([NH:18][C:19](=[O:20])[NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

참가 물질

6

반응물 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 20599951-Isocyanatoadamantane

생성물 2

HCID 114259954-(3-Adamantan-1-yl-ureido)butyric acid수율 100%HCID 114378554-(3-Adamantan-1-yl-ureido)butyric Acid Methyl Ester

실험 절차

The title compound was prepared by a procedure described in J. Med. Chem. 2004, 47, 2110. To a suspension of 4-aminobutyric acid (2.79 g, 27.1 mmol) in DMF (40 mL) was added 1-adamantyl isocyanate (1.20 g, 6.77 mmol) at room temperature. The reaction mixture was stirred for 24 h. Then 1 N HCl aqueous solution (40 mL) was added into the reaction, and the mixture was stirred for 30 min. The solid crystalline product was filtered and washed with water (20 mL) and ethyl acetate (20 mL). The resulting solid was dried in a vacuum oven to give 1.90 g (100%) of 4-(3-adamantan-1-yl-ureido)butyric acid 822 as a white solid: 1H NMR (CD3OD): 1.66-1.75 (8H, m), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.30 (2H, t, J=6.9 Hz), 3.08 (2H, q, J=6.9 Hz), 3.32 (2H, s); LC-MS (ESI) m/z calcd for C15H24N2O3 [M+H]+ 281.18, found [M+H]+ 281.25; mp 165 C. Anal. (C15H24N2O3) C, H, N.

후처리

  1. stirringthe mixture was stirred for 30 min
  2. filtrationThe solid crystalline product was filtered
  3. washwashed with water (20 mL) and ethyl acetate (20 mL)
  4. customThe resulting solid was dried in a vacuum oven

출처 및 근거

ORD 기록
ord-90a8a418ddec493f83a3dc911b9a5a16
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662910B2

반응 노트

불러오는 중…