THIAZACYCLIC AMINO COMPOUNDS AND PROCESS FOR THEIR MANUFACTURE

摘要

1281549 4-Thia-1 -azabicyclo[3,2,0]heptan-7- ones CIBA-GEIGY AG 16 July 1969 [23 July 1968 11 Dec 1968] 57065/71 Divided out of 1281548 Heading C2C Novel 4-thia- 1 -azabi cyclo[3,2,0]heptan-7-ones of the Formula I wherein R 0 is a 2-halo-C 1-7 alkyl radical, in which halo is Cl, Br or I and R is H or the acyl radical of an organic acid are prepared by reacting isocyanates of the Formula II in which Ac 0 is the same as the acyl radical in Formula I except any free functional groups therein are protected, with the appropriate 2-halo-C 1-7 alkanols of the formula R 0 OH, and, if desired, removing any protecting groups present, and/or, if desired splitting acylamino groups in resulting compounds and reacylating the free amino groups, and/or, if desired resolving resulting isomer mixtures. In addition compounds of Formula I above in which R 0 is 2-iodo-C 1-7 alkyl may be prepared from the corresponding compounds in which R 0 is 2- monochloro- or 2-monobromo-C 1-7 alkyl. 2 - Isocyanto - 3,3 - dimethyl - 6 - [phenoxyacetamido) - 4 - thio - 1 - azabicyclo[3,2,0]heptan- 7-one is obtained by heating a benzene solution of penicillin- V-azide, resulting from the treatment of penicillin-V triethylammonium salt with ethyl chloroformate and sodium azide. By similar processes penicillin-G azide 2-isocyanto- 3,3 - dimethyl - 6 - (phenylacetamido) - 4 - thia- 1 - azabicyclo[3,2,0]heptan - 7 - one, 6 - (tertbutoxycarbonylamino) - penicillanic acid azide and 2 - isocyanto - 3,3 - dimethyl - 6 - (tertbutoxycarbonylamino} - 4 - thio - 1 - azabicyclo- [3,2,0]heptan-7-one are prepared. 6 - (tert - Butoxycarbonylamino)- penicillanic acid is obtained by acylating 6-aminopenicillanic acid. Triethylamine salts of 6-aminopenicillanic acid and penicillin-G are also prepared.