L-p-Boronophenylalanine

white to off-white powder

A suspension of (S)-N-Boc-4-boronophenylalanine(5.63 g, 98.5percent pure, 17.9 mmol) in a mixture of acetone (34 ml) and water (3.8 ml) was stirred and added hydrochloric acid (37 percent, 3.8 ml) to form an acidic mixture, and the acidic mixture was stirred at 55°C for 1.5 h. HPLC analysis of the acidic mixture showed the completion of the reaction. With reference to the following Reaction Formula IV′, it is the chemical reaction formula of deprotecting the amine terminal of (S)—N-Boc-4-borono-L-phenylalanine to prepare L-BPA. The specific operation method is as follows: A reaction device was set up, using 100 mL three-necked flask. At the temperature of 2030° C., (S)—N-Boc-4-borono-L-phenylalanine (1.80 g, 5.82 mmol, 1.00 eq), water (0.63 mL) and acetone (11.30 mL) were separately added into the flask. Then HCl (17.46 mmol, 1.46 mL, 3.00 eq) was dropwise added into the reaction. After the dropwise addition was completed, the temperature of reaction was risen to 60° C., and the reaction was stirred for 4 hours. HPLC detection indicated that the reaction was already completed. The reaction liquid was concentrated under reduced pressure at 40° C. with most of acetone was rotary evaporated. The temperature was cooled down to 015° C., and the pH value was adjusted to 1.5 by NaOH solution (4M), and the solids started precipitated. The pH value was adjusted continuously to 6.2, and a large amount of white solids were precipitated, stirred for 15 minutes. The white solid was collected by filtration and drip washed with acetone (6 mL), then transferred and dried by rotary evaporating. The resulting white solid L-BPA was obtained (0.85 g, 4.07 mmol, analyzed by HPLC, 70.18percent yield, 98percent purity). The analysis results of the resulting L-BPA by HNMR were described as follows: A suspension of (S)-N-Boc-4-boronophenylalanine(5.63 g, 98.5% pure, 17.9 mmol) in a mixture of acetone (34 ml) and water (3.8 ml) was stirred and added hydrochloric acid (37 %, 3.8 ml) to form an acidic mixture, and the acidic mixture was stirred at 55C for 1.5 h. HPLC analysis of the acidic mixture showed the completion of the reaction. The acidic mixture was cooled to room temperature, and the pH value of the acidic mixture was adjusted to pH 1.5 by using sodium hydroxide aqueous solution. The acidic mixture was stirred for 30 min, and the product With reference to the following Reaction Formula IV?, it is the chemical reaction formula of deprotecting the amine terminal of (S)-N-Boc-

Molecular Weight:209.01
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:209.0859380
Monoisotopic Mass:209.0859380
Topological Polar Surface Area:104
Heavy Atom Count:15
Complexity:216
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes