ethyl 3-(cyclohexylamino)propanoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and dichloromethane. The organic layer was dried (MgSO4) and concentrated to afford 1.25 g (72%) of the title compound. The resulting mixture was then partitioned between water and dichloromethane The organic layer was dried (MgSO4) concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and dichloromethane. The organic layer was dried (MgSO4) and concentrated to afford 1.25 g (72%) of the title compound. The resulting mixture was then partitioned between water and dichloromethane The organic layer was dried (MgSO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Cyclohexylamino-propionic acid ethyl ester (1.0 g, 5.0 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.17 g, 5.02 mmol) were combined in DCM (15 mL) and diisopropylethylamine (0.81 g, 6.3 mmol) was added. After 16 h, the solution was partitioned between water and DCM and the organic layer was dried (MgSO4) and concentrated. Chromatography (0-20% EtOAc/hexanes gradient) provided 1.63 g (84%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.39 (s, 1H) 5.30 (s, 1H), 4.30 (q, 2H, J=7.1 Hz), 4.14 (q, 1H, J=7.1 Hz), 3.76-3.80 (m, 2H), 2.65-2.69 (m, 2H), 2.49 (s, 3H), 1.81-1.84 (m, 2H), 1.34-1.40 (m, 7H), 1.12-1.27 (m, 7H). the solution was partitioned between water and DCM the organic layer was dried (MgSO4) concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and DCM. The organic layer was dried (MgSO4) and concentrated to afford 1.25 g (72%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 4.14 (q, 2H, J=7.2 Hz), 2.90 (t, 2H, J=6.6 Hz), 2.50 (t, 2H, J=6.6 Hz), 1.86-1.89 (m, 2H), 1.70-1.75 (m, 2H), 1.58-1.62 (m, 2H), 1.25 (t, 1H, J=7.2 Hz). The resulting mixture was then partitioned between water and DCM The organic layer was dried (MgSO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 22 g of cyclohexylamine were added to 40 mL of ethanol, 10 g of ethyl 3-bromopropionate were added, and the mixture was heated and refluxed for two hours. The reaction system was concentrated under reduced pressure, the resulting residue was extracted with 200 mL of ethyl acetate, the organic layer was desiccated over anhydrous magnesium sulfate, and the product was then filtered and concentrated. The residue was purified by distillation under reduced pressure, and 6.3 g of N-cyclohexylmethyl β-alanine ethyl ester (yield of 57%) were obtained. 1.26 g of sodium hydroxide were dissolved in 200 mL of water, 6.3 g of N-cyclohexyl-β-alanine ethyl ester were added, and THF was added for dissolution. After stirring for one hour, the product was neutralized using Dowex 50WX4-[H+] and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized and 3.2 g of the desired product were obtained (yield of 64%). filtered the filtrate was concentrated under reduced pressure The resulting residue was recrystallized

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (0.86 g, 8.7 mmol) and 3-chloro-propionic acid ethyl ester (1.18 g, 8.67 mmol) were combined neat and K2CO3 (1.2 g, 8.7 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and dichloromethane. The organic layer was dried (MgSO4) and concentrated to afford 1.25 g (72%) of the title compound. The resulting mixture was then partitioned between water and dichloromethane The organic layer was dried (MgSO4) concentrated