Novel process for the manufacture of 4-acyloxy-3-hydroxyethyl-az

Details Novel process for the manufacture of 4-acyloxy-3-hydroxyethyl-az Novel process for the manufacture of 4-acyloxy-3-hydroxyethyl-az

1988-04-27

1990-05-22

Niebling, John F.

Chemistry: electrical and wave energy

Processes and products

204 72, 540357, 540200, C25B 302

Patent

active

049275070

ABSTRACT:
The invention relates to a novel process for the manufacture of (3R,1'R)-4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula ##STR1## in which R.sup.1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester, cyclization of the resulting .alpha.-acylaminomethyl-.beta.-hydroxybutyric acid ester to a 5,6-dihydro-1,3,4H-oxazine with inversion of the carbon atom carrying the hydroxy group, equilibration to form the preferred trans-substituted dihydrooxazine, recleaving to form the configuratively uniform .alpha.-aminomethyl-.beta.-hydroxybutyric acid, ring-closure to form the .beta.-lactam and oxidative acylation at C(4) of the .beta.-lactam. Compounds of formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention relates also to novel intermediates.

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