5-Trihalogenomethyl-4,5-dihyro-oxazole-4-carboxylic acid esters

Details 5-Trihalogenomethyl-4,5-dihyro-oxazole-4-carboxylic acid esters 5-Trihalogenomethyl-4,5-dihyro-oxazole-4-carboxylic acid esters

1975-11-26

1977-12-06

Rush, Raymond V.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260534M, C07D26314

Patent

active

040616509

ABSTRACT:
Alkyl (or aralkyl) .alpha.-isocyanoacetate is condensed with a trihalogenoacetic aldehyde or its hydrate in the presence of an amine to give trans-4-alkoxycarbonyl(or aralkyloxycarbonyl)-5-trihalogenomethyl-2-oxazoline. The oxazoline compound is hydrolyzed under acidic conditions to give threo-.gamma.,.gamma.,.gamma.-trihalogenothreonine, which is then subjected to catalytic or electrolytic reduction. The above-mentioned reactions can be carried out stereoselectively and threo-threonine is thereby obtained without by-products such as allo-threonine.

REFERENCES:
patent: 2446192 (1948-08-01), Pfister et al.
patent: 2530627 (1950-11-01), Pfister et al.
patent: 2556791 (1951-06-01), Billman et al.
Matsumoto et al., C.A. 83, 179551u, (1975), Abstract of Agric. Biol. Chem. 1975, 39(a), 1869-1873.
Bretschneider et al., C.A. 50, 305a, (1956), Abstract of Monatsh, 85, 1110-1118, (1954).

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