4-(phenylthio or phenylsulfonyl) azetidinones and process of man

Details 4-(phenylthio or phenylsulfonyl) azetidinones and process of man 4-(phenylthio or phenylsulfonyl) azetidinones and process of man

1987-09-28

1989-03-28

Berd, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540360, C07D20508, C07F 718, C07B 5300, C07B 4306

Patent

active

048165816

ABSTRACT:
The novel compounds of the formula ##STR1## wherein R.sup.11 signifies hydrogen, acyl or tri(lower alkyl)silyl, R.sup.2 signifies a phenyl group which is substituted in the o- and/or the p-position by halogen, lower alkyl, lower alkylthio or lower alkoxy and n signifies the number 0 or 2, and mixtures thereof with the corresponding optical antipodes are valuable intermediates for the manufacture of antimicrobially active penems and carbapenems which have as a common structural element a (R)-1-hydroxyethyl group in the 6-position. They can be manufactured by reacting a compound of the formula ##STR2## wherein R.sup.12 signifies acyl, tri(lower alkyl)silyl or a group of the formula --BR.sup.3 R.sup.4 and R.sup.3 and R.sup.4 have the same significance and each signify a branched-open chain, cyclic or bicyclic hydrocarbon residue with 5-10 carbon atoms or together signify an open chain or cyclic hydrocarbon residue with 5-10 carbon atoms and two free valencies and R.sup.2 has the above significance, or a mixture thereof with the corresponding optical antipode with chlorosulphonyl isocyanate and, if desired, S-oxidizing a resulting compound of formula I in which n signifies the number O and, previously or subsequently, cleaving off an acyl or tri(lower alkyl)silyl group which may be present.

REFERENCES:
K. Hirai, Chem Pharm Bull 21, 1090 (1973).
Favara, Tet. Letters 23, 3105 (1982).
Moriconi, Tet. Letters 1968, 1435.

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