Processes for preparing heterocyclic compounds including trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide and salts thereof
The present invention relates to compounds and processes for preparing compounds of Formula (I), including compounds such as trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide and salts thereof (e.g., NXL-104).
1. A process for preparing a compound of Formula (IX) comprising:
(a) treating a compound of Formula (XI)
with a source of ammonia or ammonia proxy to yield a compound of Formula (XIV):
(b) treating the compound of Formula (XIV) with a protecting group and a carbonylation agent to yield a compound of Formula (XVII):
(c) treating the compound of Formula (XVII) with a source of tetra n-butylammonium ion to yield a compound of Formula (XIX):
(d) treating the compound of Formula (XIX) with a source of sodium; wherein R8 is selected from the group consisting of substituted or unsubstituted alkyl, allyl, aryl and benzyl and R9 is a hydroxylamine protecting group.
2. The process of claim 1 , wherein R8 is selected from the group consisting of methyl, ethyl and benzyl.
3. The process of claim 1 , wherein R8 is benzyl.
4. The process of claim 1 , wherein R9 is selected from the group consisting of allyl and trialkylsilyl.
5. The process of claim 1 , wherein R9 is benzyl.
6. The process of claim 1 , comprising treating the compound of Formula (XIV) with 9-fluorenylmethoxycarbonyl.
7. The process of claim 1 , comprising treating the compound of Formula (XIV) with N,N-carbonyl diimidazole.
8. The process of claim 1 , comprising treating the compound of Formula (XVII) with a SO 3 complex.
9. ({[(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulphonyl)oxidanide prepared according to the process of claim 1 .