Acetylvaline

White crystalline powder

Solid

N-acetyl-L-valine is an L-valine derivative in which one of the amino hydrogens of L-valine has been replaced by an acetyl group. It is a N-acetyl-L-amino acid and a L-valine derivative. It is a conjugate acid of a N-acetyl-L-valinate.

L-Valine (200 g, 1.7 mol eq) is dissolved in water (500 mL) followed by the addition of NaOH (30percent, 170 mL). The mixture is cooled to 0°-5°C followed by the addition of acetic anhydride (32 ml, 1.4 eq. ). Sodium hydroxide (30percent, 34 mL) is added while keeping the temperature at 0°-5°C. Acetic anhydride and 30percent NaOH alternate additions are repeated six time while keeping the temperature (acetic anhydride, 6 x 32 mL; 30percent NaOH 6 x 34 mL). After all the additions are completed, the mixture is stirred for an additional two hours at 0°C. Hydrochloric acid (32percent, 380 mL) is added to lower the pH below 3 while keeping the temperature at 0°C. The resulting slurry is granulated for 12 hours, filter and the cake washed with HCI (0.1 N, 100 mL). The wet N-acetyl-L-valine was dried to produce 233 g (86percent yield).In a glove box, an autoclave with a 20 mL glass tube insert equipped with a magnetic stirring bar was charged with the hydrogenation substrate (1 mmol), anhydrous degassed solvent (7 mL) and the metal complex pre-catalyst (0.01 mmol). After 10 cycles of evacuation and filling with hydrogen, the autoclave was pressurised to an appropriate initial pressure of hydrogen. The reaction mixture was stirred at room temperature and after the appropriate time the autoclave was opened, the reaction mixture was filtered through silica gel, concentrated and the residue was analysed by enantioselective GC.In a glove box, an autoclave with a 20 mL glass tube insert equipped with a magnetic stirring bar was charged with the hydrogenation substrate (1 mmol), anhydrous degassed solvent (7 mL) and the metal complex pre-catalyst (0.01 mmol). After 10 cycles of evacuation and filling with hydrogen, the autoclave was pressurised to an appropriate initial pressure of hydrogen. The reaction mixture was stirred at room temperature and after the appropriate time the autoclave was opened, the reaction mixture was filtered through silica gel, concentrated and the residue was analysed by enantioselective GC.In a glove box, an autoclave with a 20 mL glass tube insert equipped with a magnetic stirring bar was charged with the hydrogenation substrate (1 mmol), anhydrous degassed solvent (7 mL) and the metal complex pre-catalyst (0.01 mmol). After 10 cycles of evacuation and filling with hydrogen, the autoclave was pressurised to an appropriate initial pressure of hydrogen. The reaction mixture was stirred at room temperature and after the appropriate time the autoclave was opened, the reaction mixture was filtered through silica gel, concentrated and the residue was analysed by enantioselective GC.In a glove box, an autoclave with a 20 mL glass tube insert equipped with a magnetic stirring bar was charged with the hydrogenation substrate (1 mmol), anhydrous degassed solvent (7 mL) and the metal complex pre-catalyst (0.01 mmol). After 10 cycles of evacuation and filling with hydrogen, the autoclave was pressurised to an appropriate initial pressure of hydrogen. The reaction mixture was stirred at room temperature and after the appropriate time the autoclave was opened, the reaction mixture was filtered through silica gel, concentrated and the residue was analysed by enantioselective GC.

Molecular Weight:159.18
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:159.08954328
Monoisotopic Mass:159.08954328
Topological Polar Surface Area:66.4
Heavy Atom Count:11
Complexity:165
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes