N-(Benzyloxycarbonyl)-β-alanine

White powder

To a mixture of 0.1 mol corresponding amino acid (3-aminopropanoic acid, 4-aminobutanoic acid, 6-aminohexanoic acid, 8-aminooctanoic acid etc.) in ethanol (25 ml) in round-bottom flask (250 mol) equipped with a magnetic stirrer and dropped funnel, a solution of NaOH (8.8 g., 0.22 mol) in 100 ml water is added and the mixture is stirred by magnetic stirrer until fully dissolved. The obtained solution is cooled to 0° C. in an ice-water bath, and benzyl chloroformate (27.4 g, 0.15 mol) is added drop wise over 30 min. The reaction mixture is stirred for 3 hours at 0° C. Subsequently, about 100 ml water is added to the reaction solution and the mixture is poured into separated funnel. The water solution is extracted with diethyl ether (3.x.50 ml). The water phase is separated and acidified with HCl (3N) to pH=1 while cooling in an ice-water bath. If a precipitate is formed, it is filtered, washed with water and dissolved in 100 ml chloroform. The chloroform solution is dried with sodium sulfate for two hours. Then the sodium sulfate is separated from the chloroform solution by filtration and the solvent is evaporated in evaporator under vacuum. The residue is washed with hexane, and dried overnight in vacuum over phosphorus pentoxide (PGeneral procedure: To a cooled (0°C) solution of the appropriate amino acid (1 eq) in NaOH 2N, a solution of benzyl chloroformate (1.1 eq) was added dropwise. The mixture was kept under vigorous stirring for 30 min. The solution was then washed with EtGeneral procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1General procedure: N-Cbz-3-aminopropanol (-OH), N-Cbz-3-aminopropanal (-CHO), and N-Cbz-3-aminopropanoic acid (-COOH) were incu-bated at maximum concentration (38, 17, and 11 mM, respectively)in 5 mL of 100 mM sodium acetate buffer (pH 5.0). The reaction wasallowed to take place under orbital agitation in a MultiThermTMdevice overnight for 19 h. Peroxide was continuously added to thereactor at 3 mM h−1

Molecular Weight:223.22
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:223.08445790
Monoisotopic Mass:223.08445790
Topological Polar Surface Area:75.6
Heavy Atom Count:16
Complexity:236
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes