Process for the stereospecific synthesis of optically pure 4-ami

Details Process for the stereospecific synthesis of optically pure 4-ami Process for the stereospecific synthesis of optically pure 4-ami

1986-07-02

1990-12-18

Springer, David B.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548344, 548543, 548538, 548498, 560 29, 560 39, 560115, 560148, 560153, 560158, 560159, 560169, 560170, 560179, 560125, 562444, 562507, 562567, 562556, 562561, 260404, 2604109, 549274, 549333, 549372, C07D20920, C07D23318, C07C 5940, C07C 5100

Patent

active

049787594

ABSTRACT:
The process described makes it possible to obtain optically pure 4-amino-3-hydroxycarboxylic acids by means of a series of stereoselective steps. The starting material is an alpha-amino acid in the L or D configuration, with which Meldrum's acid is reacted. The resulting pyrrolone derivative is reduced prior to opening of the pyrrolidine ring. The invention also relates to the new products obtained by the said process and to the pyrrolone derivatives obtained as intermediates.

REFERENCES:
patent: 3503993 (1970-03-01), Blame
patent: 4264771 (1981-04-01), Steglich et al.
patent: 4547516 (1985-10-01), Bellini et al.
Porter et al., "Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans", Int. J. Peptide Protein Res. 30, 1987, pp. 13-21.
Albertson, "The Synthesis of Amino Acids from Ethyl Acetamidomalonate and Ethyl Acetamidocyanoacetate. III. The Use of Primary Halides", J.Am. Chem. Soc., vol. 68, 1946, pp. 450-453.
Snyder et al., "Synthetic Amino Acids Syntheses from Acetamidomalonic Ester", J. Am. Chem. Soc., vol. 67, 1945, pp. 310-312.
The Merk Index, 9th Ed., 1976, Organic Name Reactions, ONR-85-86.
Tarbell et al., "New Method To Prepare N-t-Butoxycarbonyl Derivatives and the Corresponding Sulfur Analogs from Di-t-Butyl Dicarbonate or di-t-Butyl Dithiol Dicarbonates and Amino Acids", Proc. Nat. Acad. Sci., U.S.A., vol. 69, No. 3, 3/72, pp. 730-732.
Roberts et al., Chimie Organique Moderne, Paris, 1967, pp. 521-522.
Katsuki et al., Bull. of Chem. Soc. of Japan, vol. 49(11), pp. 3287-3290 (1976).

Affiliated with

Also associated with

Rating

Process for the stereospecific synthesis of optically pure 4-ami does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the stereospecific synthesis of optically pure 4-ami, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the stereospecific synthesis of optically pure 4-ami will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1426379