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US 5,859,284 AGranted
Preparation of carbocyclic compounds
AssigneeGilead Sciences, Inc.
InventorsKenneth M. Kent, Choung U. Kim, Lawrence R. McGee, John D. Munger, Jr., Ernest J. Prisbe, Michael J. Postich, John C. Rohloff, Daphne E. St. John, Matthew A. Williams, Lijun Zhang
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Abstract
The present invention provides new synthetic methods and compositions. In particular, new methods of preparing intermediates useful in the synthesis of neuraminidase inhibitors and compositions useful as intermediates that are themselves useful in the synthesis of neuraminidase inhibitors are provided.
Claims3
A process for preparation of compounds of the formula:
- ##STR42## wherein:
- R.sup.2 is a carboxylic acid protecting group;
- R.sup.3 is a hydroxy protecting group;
- R.sup.4 is --C(R.sup.30).sub.3 ;
- R.sup.5 is H or R.sup.3 ;
- R.sup.7 is H or an amino protecting group;
- R.sup.8 is H or R.sup.2 ;
- R.sup.9 is H or a thiol protecting group;
- each R.sup.20 is independently H or an alkyl of 1 to 12 carbon atoms;
- each R.sup.21 is independently R.sup.20, Br, Cl, F, I, CN, NO.sub.2 or N.sub.3 ;
- each R.sup.22 is independently F, Cl, Br, I, --CN, N.sub.3, --NO.sub.2, --OR.sup.5, --OR.sup.20, --N(R.sup.20).sub.2, --N(R.sup.20)(R.sup.7), --N(R.sup.7).sub.2, --SR.sup.20, --SR.sup.9, --S(O)R.sup.20, --S(O).sub.2 R.sup.20, --S(O)OR.sup.20, --S(O)OR.sup.8, --S(O).sub.2 OR.sup.20, --S(O).sub.2 OR.sup.8, --C(O)OR.sup.20, --C(O)OR.sup.8, --OC(O)R.sup.20, --N(R.sup.20)(C(O)R.sup.20), --N(R.sup.7)(C(O)R.sup.20), --N(R.sup.20)(C(O)OR.sup.20), --N(R.sup.7)(C(O)OR.sup.20), --C(O)N(R.sup.20).sub.2, --C(O)N(R.sup.7)(R.sup.20), --C(O)N(R.sup.7).sub.2, --C(NR.sup.20)(N(R.sup.20).sub.2), --C(N(R.sup.7))(N(R.sup.20).sub.2), --C(N(R.sup.20))(N(R.sup.20)(R.sup.7)), --C(N(R.sup.7))(N(R.sup.20)(R.sup. 7)), --C(N(R.sup.20))(N(R.sup.7).sub.2), --C(N(R.sup.7))(N(R.sup.7).sub.2), --N(R.sup.20)C(N(R.sup.20))(N(R.sup.20).sub.2), --N(R.sup.20)C(N(R.sup.20))(N(R.sup.20)(R.sup.7)), --N(R.sup.20)C(N(R.sup.7))(N(R.sup.20).sub.2), --N(R.sup.7)C(N(R.sup.20))(N(R.sup.20).sub.2), --N(R.sup.7)C(N(R.sup.7))(N(R.sup.20).sub.2), --N(R.sup.7)C(N(R.sup.20))(N(R.sup.20)(R.sup.7)), --N(R.sup.20)C(N(R.sup.7))(N(R.sup.20)(R.sup.7)), --N(R.sup.20)C(N(R.sup.20))(N(R.sup.7).sub.2), --N(R.sup.7)C(N(R.sup.7))(N(R.sup.20)(R.sup.7)), --N(R.sup.7)C(N(R.sup.20))(N(R.sup.7).sub.2), --N(R.sup.20)C(N(R.sup.7))(N(R.sup.7).sub.2), --N(R.sup.7)C(N(R.sup.7))(N(R.sup.7).sub.2), .dbd.O, .dbd.S, .dbd.N(R.sup.20), .dbd.N(R.sup.7) or W;
- R.sup.23 is independently alkyl of 1 to 11 carbon atoms, alkenyl of 2 to 11 carbon atoms, or alkynyl of 2 to 11 carbon-atoms;
- R.sup.24 is independently R.sup.23 wherein each R.sup.23 is substituted with 0 to 3 R.sup.22 groups;
- R.sup.24a is independently alkylene of 1 to 11 carbon atoms, alkenylene of 2 to 11 carbon atoms, or alkynylene of 2-11 carbon atoms any one of which alkylene, alkenylene or alkynylene is substituted with 0-3 R.sup.22 groups;
- compound;
- R.sup.28 is independently alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms, or alkynyl of 2 to 12 carbon atoms;
- R.sup.29 is independently R.sup.22 or R.sup.28 wherein each R.sup.28 is substituted with 0 to 3 R.sup.22 groups;
- each R.sup.30 is independently H, R.sup.24, W or R.sup.24a -W;
- and
- W is carbocycle or heterocycle wherein any one of which carbocycle or heterocycle is substituted with 0 to 3 R.sup.29 groups;
- which process comprises reaction of a compound of the formula:
- ##STR43## wherein R.sup.31 is a ketal or acetal, with a lewis acid reagent;
- provided that R.sup.4, taken as a whole, contains:
- 0to 3 W groups substituted with 0 to 3 R.sup.29 groups;
- and
- 1 to 12 carbon atoms substituted with 0 to 3 R.sup.22 groups.
23 more elements
Dependencies are inferred from the claim text.