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

HRID 1444640Notes

Reaction equation

HRID 1444640 reaction equation
[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

Participants

6

Reactant 4

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

Product 2

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-90a8a418ddec493f83a3dc911b9a5a16
Source dataset
uspto-grants-2010_02
Patent number
US07662910B2

Reaction notes

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