Optically active N-substituted phenylalaninols and use thereof

Details Optically active N-substituted phenylalaninols and use thereof Optically active N-substituted phenylalaninols and use thereof

1983-09-23

1985-08-20

Love, Ethel G.

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

Organic compounds

Amino nitrogen containing

549443, 564336, 564373, C07C 9102, C07D31744

Patent

active

045366012

ABSTRACT:
Optically active N-substituted phenylalaninols of the formula (I): ##STR1## wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.

REFERENCES:
patent: 3804899 (1974-04-01), Ebnother et al.
patent: 4224457 (1980-09-01), Iwao et al.
patent: 4294775 (1981-10-01), McKinnie
patent: 4325886 (1982-04-01), Ohashi et al.
patent: 4372969 (1983-02-01), Lafon
Agr, Biol. Chem., 37(7) 1713-1716, 1973.
Chem. Abstr., 95 (1981), pp. 618, 6512b and ibid, pp. 624, 24281e.

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