Process for preparing benzoxazolyl propionic acid derivatives

Details Process for preparing benzoxazolyl propionic acid derivatives Process for preparing benzoxazolyl propionic acid derivatives

1979-07-26

1981-12-08

Sutto, Anton H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26356

Patent

active

043049184

ABSTRACT:
The application describes a process for preparing 2-phenyl derivatives of benzoxazolyl propionic acid of formula ##STR1## in which X is H, Cl, Br, F, or a linear or branched alkyl or 1 to 6 carbon atoms. The process starts from 3-nitro-4-hydroxyphenyl-.alpha.-methyl-acetonitrile which is hydrolysed in the presence of a strong acid, the 3-nitro-4-hydroxyphenyl-.alpha.-methylacetic acid thus obtained is hydrogenated in the presence of Pd on carbon, and the 3-amino-4-hydroxyphenyl-.alpha.-methylacetic acid deriving therefrom is first reacted with benzoyl chloride or with para-substituted benzoyl chloride in the presence of an alkaline base, and then with 85% phosphoric acid to complete the formation of the oxazolinic ring.

REFERENCES:
patent: 2995564 (1961-08-01), Duennenberger et al.
patent: 3471508 (1969-10-01), Sarett et al.
patent: 3478046 (1969-11-01), Sarett et al.
patent: 4100168 (1978-07-01), Dunwell et al.
Cram et al., "Organic Chemistry", 2nd Edition, (1964), p. 307.
Wagner et al., "Synthetic Organic Chemistry", (1953), pp. 412, 654 and 566.
Elderfield, "Heterocyclic Compounds", vol. 5, (1957), p. 422.

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