4-Aminocyclohexanecarboxylic acid

A mixture of The amino acid (22.45 mmol, 1.0 eq) was suspended in MeOH (20 mL per 10 mmol of amino acid) and reaction mixture was cooled to 0 °C. Thionyl chloride (4 eq) was carefully added dropwise and the reaction mixture was left to stir for 12h at room temperature. The mixture was concentrated under reduced pressure and diethylether was added (10 mL per 10 mmol of amino acid). Precipitate was collected and washed with cooled diethyether (10 mL per 10 mmol of amino acid).To a solution of (1R, 4R)-4-aminocyclohexane-1-carboxylic acid (2 g, 13 mmol) in N, N-dimethyl formamide (10 mL) was added Boc anhydride (5 g, 20 mmol) and triethylamine (4.2 g, 13 mmol). Then, the resulting reaction mixture was stirred at ambient temperature for 18 h. Completion of the reaction was confirmed by GCMS. The product was isolated to afford (1R, 4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid (2.5 g, 95percent) as a pale yellow solid. GCMS m/z 243 [M]+.To a stirred solution of To a solution of (1R, 4R)-4-aminocyclohexane-1-carboxylic acid (2 g, 13 mmol) in N, N-dimethyl formamide (10 mL) was added Boc anhydride (5 g, 20 mmol) and triethylamine (4.2 g, 13 mmol). Then, the resulting reaction mixture was stirred at ambient temperature for 18 h. Completion of the reaction was confirmed by GCMS. The product was isolated to afford (1R, 4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid (2.5 g, 95percent) as a pale yellow solid. GCMS m/z 243 [M]+.To a stirred solution of Xa is selected among the following amino acid residues:...4-(4-aminophenyl)butanoic acid;3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;...of the following groups:-(Gly)n-, n ranging from 1 to 10;-(Pro)n-, n ranging from 1 to 10;NH2-(CH2)n-COON, n ranging from 1 to 10;NH2-(CH2-CH2-O)m-CH2CH2COOH, m ranging from 3 to 6;...3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;...ing amino acid residues:-(Gly)n-, n ranging from 1 to 10;-(Pro)n-, n ranging from 1 to 10;NH2-(CH2)n-COON, n ranging from 1 to 10;NH2-(CH2-CH2-O)m-CH2CH2COOH, m ranging from 3 to 6;...3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;Xe is chosen from the following amino acid residues:NH2-(CH2)-COOH, n varying from 1 to 10;NH2-(CH2-CH2-O)m-CH2CH2COOH, m varying from 3 to 6;...3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;Xc is chosen from the following amino acid residues:...4-(4-aminophenyl)butanoic acid;3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;Xc is chosen from the following amino acid residues:...4-(4-aminophenyl)butanoic acid;3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2aminoethyl)-1-carboxymethyl-piperazine;Xf is chosen from the following amino acid residues:NH2-(CH2)-COOH, n varying from 1 to 10;NH2-(CH2-CH2-O)m-CH2CH2COOH, m varying from 3 to 6;...3-(4-aminophenyl)propanoic acid;4-aminophenylacetic acid;4-(2-aminoethyl)-1-carboxymethyl-piperazine;p-Aminobenzoic acid (10.0 g, 0.07mol, leq.), 5 percent Ru/C (2, 50 g) and 10percent NaOH (lOO.OmL) were mixed in autoclave. The mixture was stirred at 100°C under 15 bar of hydrogen. After 20h of stirring no Starting material was observed on TLC (DCM/MeOH/NH3 = 5/5/1, v/v/v, stain: ninhydrine). According to the NMR - full conversion and cis:trans ratio = 1 :4.6 . Reaction was stopped.

Molecular Weight:143.18
XLogP3:-2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:143.094628657
Monoisotopic Mass:143.094628657
Topological Polar Surface Area:63.3
Heavy Atom Count:10
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes