Process for the preparation of 7-amino-1-dethia-1-oxa-3-hydroxym

Details Process for the preparation of 7-amino-1-dethia-1-oxa-3-hydroxym Process for the preparation of 7-amino-1-dethia-1-oxa-3-hydroxym

1983-06-20

1985-01-29

Raymond, Richard L.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

2602455, 2603309, 544 95, 544374, 546275, 548147, 549273, C07D49804

Patent

active

044967233

ABSTRACT:
Compounds which themselves are antibacterially active and/or which are useful as intermediates for producing antibacterially active materials such as penicillins and cephalosporins are obtained by the following syntheses:
Benzyl-2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2(N-formyl-1)-aminoacetate to benzyl-2,2-dimethylspiro-[1,3-dioxane-5,5'-1',3-thiazoline]-4'-carboxylate to benzyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)-2[N-(methylthiomethylene)-amino] acetate to benzyl 2-(trans-3-azido-4-methylthio-2-oxo-1-azetidinyl)-2-(2,2-dimethyl-1,3-diox an-5-ylidene) acetate to benzyl 2(trans-3-benzoylamino-4-methylthio-1-azetidinyl)-2-(2,2-dimethyl-1,3-diox an-5-ylidene) acetate to either (1) benzyl 2-(7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-2-(2,2-dime thyl-1.3-dioxan-5-ylidene)acetate or (2) benzyl 2-(trans-3-benzoylamino-4-chloro-1-azetidinyl)-2-(2,2-dimethyl-1,3-dioxan- 5-ylidene) acetate and then to the product benzyl-7-benzoylamino-1-dethia-1-oxa-3-hydroxymethyl-cephem-4-carboxylate.

REFERENCES:
Narisada et al., J. Antibiotics, vol. 35 (1982) p. 463.

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