(1S,3R)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclopentanecarboxylic acid

white powder or chunks

The acid prepared in Step A (230 g, 1.0 mol) and 10 percent Pd/C (5.0 G) in 500 ML of methanol on a Parr shaker was HYDROGENATED under 50 psi of hydrogen for 1 h. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated and dried under vacuum. The title compound was obtained as a light yellow solid (230 g, 99 percent). LC-MS for C11H19N04 [M+H+] CALCULATED 230, found 230.The acid (Step A, Procedure A, Intermediate 5) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol on a Parr shaker was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtered, the filtrate was evaporated and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99 percent). LC-MS for C1 lH19NO4 [MF calculated 230, found 230.Step B; The solution of the acid (Step A, Procedure A, Intermediate 4) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. The filtrate was evaporated to dryness and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99percent). LC-MS for CThe acid (Step A, Procedure A, Intermediate 5) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol on a Parr shaker was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtered, the filtrate was evaporated and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99 percent). LC-MS for C11H19NO4 [M+H+] calculated 230, found 230.di-tert-l3utyl dicarbonate (1.25 g, 5.75 mmol) and DIPEA (2.61 mE, 15.0 mmol) were added to a solution of (1 S, 3R)-3-aminocyclopentanecarboxylic acid (0.646 g, 5.0 mmol) in 1, 4-dioxane (5 mE) and water (5 mE) and the resulting mixture was stirred at RT for 3 h. The reaction mixture was acidified to pH 2 using 1 M aqueous HC1 and extracted with DCM (x4). The combined organic extractswere passed through a phase separator cartridge and con-centrated in-vacuo to give (1 S, 3R)-3-[(tert-butoxycarbonyl) amino]cyclopentanecarboxylic acid (1.13 g, 99percent). ‘H NMR (400 MHz, CDC13) ö: 1.44 (s, 9H), 1.56-2.06 (m, 5H), 2.16-2.33 (m, 1H), 2.79-2.93 (m, 1H), 3.87-4.18 (m, 1H), 4.86 (bt s., 1H). One exchangeable proton not observed.Step C: Preparation of (1S, 3R)-Cyclopentanecarboxylic acid, 3-[[(1, 1-dimethylethoxy)carbonyl]amino]. Aqueous potassium carbonate (2.20 g, 15.7 mmol) in water (20 ml) was added to a suspension of (1S, 3R)-3-aminocyclopentanecarboxylic acid hydrochloride (1.30 g, 7.85 mmol) in THF (20 ml) at 0° C., stirred for 15 min and Boc-anhydride (2.70 ml, 11.8 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 20 h. The reaction mixture was acidified with 10percent acetic acid to a pH of 4.0-5.0 and extracted with ethyl acetate (2.x.30 ml). The combined organic layer was washed successively with water, brine, dried over anhydrous sodium sulfate and concentrated to afford 1.30 g (72.2percent) of (1S, 3R)-cyclopentanecarboxylic acid, 3-[[(1, 1-dimethylethoxy)carbonyl]amino] as pale yellow liquid.

Molecular Weight:229.27
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:229.13140809
Monoisotopic Mass:229.13140809
Topological Polar Surface Area:75.6
Heavy Atom Count:16
Complexity:282
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes