Process for preparing 5-arylhydantoins using 5-hydantoin, a halo

Details Process for preparing 5-arylhydantoins using 5-hydantoin, a halo Process for preparing 5-arylhydantoins using 5-hydantoin, a halo

1994-10-06

1997-02-25

Higel, Floyd D.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540314, 5483171, 5483175, 5483191, 5483205, 562451, C07D23376, C07D23354, C07D23378, C07D23372, C07D23386

Patent

active

056060718

ABSTRACT:
The present invention provides a novel process for the preparation of 5-arylhydantoins as an important intermediate of (D)-arylglycines (e.g., (D)-p-hydroxyphenyl-glycine) useful for the synthesis of semisynthetic penicillines and cephalosporins, the process comprising (i) reacting a 5-unsubstituted hydantoin compound with a halogenating agent and (ii) reacting the resulting product with a p-unsubstituted phenol compound, the hydroxy group of which may be protected, to substitute the 5-position of the hydantoin compound with the phenol compound at the para position.

REFERENCES:
patent: 2564649 (1951-08-01), Rogers
patent: 2626263 (1953-01-01), Gaudry
patent: 3939175 (1976-02-01), Schmidt et al.
patent: 4044019 (1977-08-01), Schmidt et al.
patent: 4066616 (1978-01-01), Lind
patent: 4440934 (1984-04-01), Kim et al.
patent: 4871391 (1989-10-01), Wee et al.
Ware, Elinor; The Chemistry of the Hydantoins, Nov. 3, 1949, pp. 403, 434, 435, 456, 461.
Henson, Edward B., et al.; Synthesis of D,L,.beta.-Carboxyaspartic Acid From Hydantoin-5-Malonic Acid Diethyl Ester, Aug. 7, 1980, pp. 2561-2562.

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