Production method of β-amino-α-hydroxycarboxylic acid

A method for producing a β-amino-α-hydroxycarboxylic acid of formula (1)

• wherein A is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, each optionally having substituent(s) and optionally having heteroatom(s) in the carbon skeleton, and * indicates an asymmetric carbon atom, provided that, when the configuration of the 2-position and 3-position of said β-amino-α-hydroxycarboxylic acid of formula (1) is (2R, 3S), (2S,3R), (2S,3S) or (2R,3R), the configuration of the 2-position and 3-position of N-carbamate protected β-aminoepoxide of formula (2) below is (2S,3S), (2R,3R), (2R,3S) or (2S,3R), respectively, the configuration of the 4-position and 5-position of the oxazolidin-2-one compound of formula (3) below is (4S,5R), (4R,5S), (4S,5S) or (4R,5R) respectively, and the configuration of the 4-position and 5-position of oxazolidin-2-one compound of formula (4) below is (4S,5R), (4R,5S), (4S,5S) or (4R,5R) respectively:
• said method comprising the following steps (a)-(c)
• (a) treating an N-carbamate protected β-aminoepoxide of formula (2)
• wherein R1 is a tert-butyl group or a benzyl group, and A and * are as defined above, with an acid to give an oxazolidin-2-one compound of formula (3)
• wherein A and * are as defined above,
• (b) oxidizing said oxazolidin-2-one compound of formula (3) in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an oxazolidin-2-one compound of formula (4)
• wherein A and * are as defined above,
• (c) treating said oxazolidin-2-one compound of formula (4) with a base to give said β-amino-α-hydroxycarboxylic acid of formula (1).