ChemicalBook CAS DataBase List 4-BORONO-L-PHENYLALANINE

4-BORONO-L-PHENYLALANINE synthesis

8synthesis methods

Product Name:4-BORONO-L-PHENYLALANINE
CAS Number:76410-58-7
Molecular formula:C9H12BNO4
Molecular Weight:209.01

(S)-3-(4-boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid

119771-23-2
81 suppliers
$70.00/5g

76410-58-7
167 suppliers
$21.00/100mg

Yield:76410-58-7 93.2%

Reaction Conditions:

with hydrogenchloride in water;acetone at 55; for 1.5 h;

Steps:

1 Preparation of 4-borono-L-phenylalanine (L-BPA) from (S)-N-Boc-4-boronophenylalanine
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 55°C 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 4-borono-L-phenylalanine started to precipitate during this period.
The pH value of the acidic mixture was readjusted to pH 6.2 by using sodium hydroxide aqueous solution, and the acidic mixture was stirred overnight at room temperature.
The acidic mixture was filtered to obtain solid 4-borono-L-phenylalanine.

References:

Taiwan Biotech Co., Ltd.;Sheu, Kuen-Wang;Huang, Shu-Fen;Shaw, Chia-Cheng EP2865682, 2015, A1 Location in patent:Paragraph 0077; 0078

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