BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID

White crystalline powder

4.3: After the completion of the separation, ethyl acetate was added to extract D-isomer to obtain an aqueous solution of L-2-amino-4bromo-4-pentenoic acid, 5 L of acetone and 120 g of di-tert-butyl dicarbonate were added, and the aqueous sodium carbonate solution was maintained. pH 8-9, 20 °C reaction 5 hours.After completion of the reaction, the mixture was acidified with 3M hydrochloric acid, extracted with ethyl acetate, dried, and crystallized to obtain 64 g of N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid as a solid.HPLC = 98.84percent, total yield 43.5percent, 2.3: After completion of the separation, an aqueous solution of L-2-amino-4bromo-4-pentenoic acid is obtained after extraction of the D isomer with ether.3L of dioxane and 70g of t-butyl chloroformate were added, and the aqueous sodium carbonate solution was maintained at pH 8-9 and reacted at 30°C for 4 hours. After the reaction was acidified by 3M hydrochloric acid, ethyl acetate was extracted, dried, and crystallized.70 g of a solid of N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid was obtained.3.3: After the completion of the separation, ethyl acetate was added to extract the D isomer to obtain an aqueous solution of L-2-amino-4bromo-4-pentenoic acid.4 L of tetrahydrofuran and 120 g of tert-butyl N-diazocarbamate, aqueous sodium carbonate solution maintained pH 8-9, and reacted at 20° C. for 5 hours. After completion of the reaction, the residue was acidified with 5percent citric acid, extracted with ethyl acetate, dried, and crystallized to obtain 66 g of solid N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid. HPLC = 99.89percent with a total yield of 44.8percent.

Molecular Weight:294.14
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:293.02627
Monoisotopic Mass:293.02627
Topological Polar Surface Area:75.6
Heavy Atom Count:16
Complexity:296
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes