Process for the preparation of aminolactone carboxylic acid

Details Process for the preparation of aminolactone carboxylic acid Process for the preparation of aminolactone carboxylic acid

1983-06-27

1985-12-17

Milestone, Norma S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260239A, 2603309, C07D30930

Patent

active

045594066

ABSTRACT:
The invention relates to a process for the preparation of the compound of the formula I, ##STR1## which comprises (a.sub.1) splitting off the ethylene ketal protecting group from the azetidinone derivative of the formula IVa, ##STR2## reducing the compound of the formula III thus obtained, ##STR3## treating the resulting compound of the formula II ##STR4## with concentrated aqueous hydrogen chloride solution; or (a.sub.2) reducing the compound of the formula III, treating the compound of the formula II thus obtained with concentrated aqueous hydrogen chloride solution; or (a.sub.3) treating the compound of the formula II with concentrated aqueous hydrogen chloride solution; and isolating the compound of the formula I thus obtained from the reaction mixture. The compound of the formula I is useful as an intermediate in the production of thienamycin, a highly potent antibiotic.

REFERENCES:
patent: 4269772 (1981-05-01), Melillo et al.
patent: 4282148 (1981-08-01), Liu et al.
patent: 4287123 (1981-09-01), Liu et al.
patent: 4344885 (1982-08-01), Liu et al.
patent: 4349687 (1982-09-01), Liu et al.
patent: 4360684 (1982-11-01), Cvetovich et al.
Houben-Weyl, Methoden der Organischen Chemie, vol. VI/2 (1963) pp. 588-589.
D. G. Melillo et al., Tetrahedron Letters, vol. 21 (1980) pp. 2783-2786.

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