Process for the preparation of N-hydroxy-alpha-amino acid amides

Details Process for the preparation of N-hydroxy-alpha-amino acid amides Process for the preparation of N-hydroxy-alpha-amino acid amides

1990-09-20

1992-03-31

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548496, 548497, 564160, 564164, 564165, 564198, C07D23364, C07D20920, C07C23112

Patent

active

051010364

ABSTRACT:
The invention relates to a process for the preparation of N-hydroxy-alpha-amino acids and the derivatives thereof by reacting a derivative of an alpha-amino acid with an aromatic aldehyde to form a Schiff base, oxidizing the Schiff base to an oxaziridine and converting the oxaziridine into the corresponding N-hydroxy-alpha-amino acid derivative and, if so desired, converting that derivative into the acid or a different derivative, in which an alpha-amino acid amide is used as starting material.

REFERENCES:
patent: 3064007 (1962-11-01), Krimm et al.
patent: 4172846 (1979-10-01), Boesten
patent: 4847412 (1989-07-01), Boesten et al.
Nikishin et al., "Direct Oxidation of Alkanoic Acids and their Amides to .tau.-Lactones by Peroxidsulphate-Containing Systems", J. Chem. Soc. Perkin Trans. II (1983), pp. 595-601.
Matlin et al., "The Oxidation of Trimethylsilylated Amides to Hydroxamic Acids", J.C.S. Perkin I, 1 (10) (1979), pp. 2481-2487.
Sondu et al., "Kinetics and Mechanism of Oxidation of Some Aliphatic Amides by Ce(IV) in Perchloric Acid", Oxidation Communications 7, Nos. 3-4 (1984) pp. 223-233.
Grundke et al., Synthesis, (12), 1115-1116, (1987).
March, "Advanced Organic Chemistry", 2nd ed., McGraw-Hill, New York, 1977, p. 1107.
Polonski et al., I, Tetrahedron Letters, (28), 2453-2456, (1974).
Polonski et al., II, Chemical Abstracts, vol. 93, No. 26754u (1980).
Polonski et al., III, Chemical Abstracts, vol. 90, No. 87876v (1979).

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