tert-butyl N-[3-(tert-butylamino)-3-oxopropyl]carbamate

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

Procedure: (2-tert-Butylcarbamoyl-ethyl)-carbamic acid tert-butyl ester (0.65 g, 2.64 mmol) is dissolved in trifluoroacetic acid (3.5 ml) and allowed to stir at room temperature under an inert atmosphere for 3 hours. The solvent is removed in vacuo to yield the titled compound as a TFA salt which is used crude in the next step: The solvent is removed in vacuo

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

Procedure: (2-tert-Butylcarbamoyl-ethyl)-carbamic acid tert-butyl ester (0.65 g, 2.64 mmol) is dissolved in trifluoroacetic acid (3.5 ml) and allowed to stir at room temperature under an inert atmosphere for 3 hours. The solvent is removed in vacuo to yield the titled compound as a TFA salt which is used crude in the next step: The solvent is removed in vacuo

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

Procedure: A solution of 3-tert-Butoxycarbonylamino-propionic acid (0.5 g, 2.64 mmol) in DCM (5 ml) under an inert atmosphere is treated with 1-hydroxy-7-azabenzatriazole (0.108 g, 0.79 mmol) followed by water soluble carbodiimide (0.491 g, 3.17 mnol) and tert-butylamine (0.305 ml, 2.91 mmol). The reaction mixture is stirred at room temperature for 3 hours and then citric acid (10 ml, 0.5 M) is added to the solution and extracted with DCM (2×10 ml). The combined organic layers are washed with brine (10 ml) and dried over MgSO4. After filtration, the solvent is removed in vacuo to yield the titled compound as an oil. extracted with DCM (2×10 ml) The combined organic layers are washed with brine (10 ml) dried over MgSO4 After filtration the solvent is removed in vacuo

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

Procedure: BOC-Beta-Ala-OH (25 g, 0.132 mol) is dissolved in DCM (500 ml) and then treated with EDC1 (30.4 g, 0.59 mol) followed by t-butylamine (16.7 ml, 0.159 mol) to give a pale orange solution. The reaction mixture is stirred at room temperature overnight and then partitioned between 20% citric acid (400 ml) and DCM (250 ml). The organic portion is separated and washed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml), dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid. treated with EDC1 (30.4 g, 0.59 mol) to give a pale orange solution partitioned between 20% citric acid (400 ml) and DCM (250 ml) The organic portion is separated washed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml) dried over MgSO4 concentrated in vacuo

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

Procedure: To a mixture of tert-butylamine (210 μl; 2 mmol; 1 eq) and boc-beta-alanine (416.3 mg; 2.20 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (832 μl; 6 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1 533 mg; 6 mmol; 3 eq). The mixture is stirred overnight at RT. The reaction is followed by TLC (cyclohexane/EtOAc 1:1). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated, to give 639 mg of an orange oil which is purified by flash chromatography (cyclohexane/EtOAc gradient, from 9/1 to 1/1 over 30 min). The title product is isolated as a slightly yellow solid (467.7 mg; 96%). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution The organic layer is dried over Na2SO4 filtered concentrated

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

Procedure: (2-tert-Butylcarbamoyl-ethyl)-carbamic acid tert-butyl ester (0.65 g, 2.64 mmol) is dissolved in trifluoroacetic acid (3.5 ml) and allowed to stir at room temperature under an inert atmosphere for 3 hours. The solvent is removed in vacuo to yield the titled compound as a TFA salt which is used crude in the next step: The solvent is removed in vacuo

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

Procedure: A solution of 3-tert-Butoxycarbonylamino-propionic acid (0.5 g, 2.64 mmol) in DCM (5 ml) under an inert atmosphere is treated with 1-hydroxy-7-azabenzatriazole (0.108 g, 0.79 mmol) followed by water soluble carbodiimide (0.491 g, 3.17 mnol) and tert-butylamine (0.305 ml, 2.91 mmol). The reaction mixture is stirred at room temperature for 3 hours and then citric acid (10 ml, 0.5 M) is added to the solution and extracted with DCM (2×10 ml). The combined organic layers are washed with brine (10 ml) and dried over MgSO4. After filtration, the solvent is removed in vacuo to yield the titled compound as an oil. extracted with DCM (2×10 ml) The combined organic layers are washed with brine (10 ml) dried over MgSO4 After filtration the solvent is removed in vacuo

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

Procedure: BOC-Beta-Ala-OH (25 g, 0.132 mol) is dissolved in DCM (500 ml) and then treated with EDC1 (30.4 g, 0.59 mol) followed by t-butylamine (16.7 ml, 0.159 mol) to give a pale orange solution. The reaction mixture is stirred at room temperature overnight and then partitioned between 20% citric acid (400 ml) and DCM (250 ml). The organic portion is separated and washed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml), dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid. treated with EDC1 (30.4 g, 0.59 mol) to give a pale orange solution partitioned between 20% citric acid (400 ml) and DCM (250 ml) The organic portion is separated washed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml) dried over MgSO4 concentrated in vacuo