153201-10-6Relevant articles and documents
Equilibrium control in bromomethylation: An expedient route to 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA)
Begtrup,Slok
, p. 861 - 863 (1993)
The excitatory amino acid 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) has been prepared in gram quantities in 42% total yield by a three-step procedure from 3-hydroxy-5-methylisoxazole. It is shown how bromomethylation may be optimized through control of the involved equilibria and how N-protecting methoxymethyl groups can be removed.
An efficient and general enantioselective synthesis of some isoxazole- containing analogues of the neuroexcitant glutamic acid
Pajouhesh, Hassan,Curry, Kenneth
, p. 2757 - 2760 (2007/10/03)
Isoxazole amino acids are an important class of neuroexcitant which are difficult to prepare in enantiopure form. Diastereoselective alkylation of the enantiomerically pure glycine derivative, tert-butoxycarbonyl-2-(tert- butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI) with 4- bromomethyl-2-methoxymethyl-5-methylisoxazolin-5-one 5 or 5-bromomethyl-4- bromo-3-methoxyisoxazole, gives intermediates which under mild hydrolysis conditions produce the amino acids (S)- and (R)-bromohomoibotenic acid and (S)- and (R)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid with e.e. >99%.
