Claims
- 1. A process for preparing a compound of formula V
- 2. A process according to claim 1 wherein the coupling step is carried out in the presence of β-chlorodiisopinocamphenylborane, triethylamine and diethyl ether, at a temperature of between −78° C. and −20° C.
- 3. A process according to claim 1 wherein the reduction step is carried out in the presence of tetramethylammonium triacetoxyborohydride, acetonitrile and acetic acid, at a temperature of between −40° C. and −10° C.
- 4. A process according to claim 1 wherein the lactonization and deprotection of the acid labile hydroxyl protecting groups step is carried out in the presence of aqueous hydrogen chloride, methanol and tetrahydrofuran, at a temperature of between −20° C. and 40° C.
- 5. A compound of formula I:
- 6. A compound according to claim 5 of formula Ia:
- 7. A compound according to claim 6 of formula Ib:
- 8. A compound according to claim 7 of formula Ic:
- 9. A compound according to claim 8 which is (2R,3S,4R)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N-methoxy-N,2,4-trimethyl-5-oxo-hexanamide having the formula
- 10. A process for preparing a compound of formula I according to claim 5 which comprises, in a first step, addition of a methyl or ethyl organometallic reagent to an aldehyde of formula VI
- 11. A process according to claim 10 wherein the addition step is carried out in the presence of methylmagnesium bromide and diethyl ether, at a temperature of between −78° C. and 40° C.
- 12. A process according to claim 10 wherein the oxidation step is carried out in the presence of sulfur trioxide-pyridine complex, triethylamine and dichloromethane, at a temperature of between −78° C. and 40° C.
- 13. A compound of formula III:
- 14. A compound according to claim 13 which is (2R,3S,4R,7S,8Z,10S,11S,12S,13Z, 16S,17R,18R,19S,20S,21 E)-19-[(aminocarbonyl)oxy]-3,11,17-tris[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-7-hydroxy-N-methoxy-N,2,4,10,12,14,16,18,20-nonamethyl-5-oxo-8,13,21,23-tetracosatetraenamide having the formula
- 15. A compound of formula IV:
- 16. A compound according to claim 15 which is (2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z,16S,17R,18R,19S,20S,21E)-19-[(aminocarbonyl)oxy]-3,11,17-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,7-dihydroxy-N-methoxy-N,2,4,10,12,14,16,18,20-nonamethyl-8,13,21,23-tetracosatetraenamide having the formula
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Application No. 60/xxx,xxx, filed Aug. 7, 2000, which was converted from U.S. application Ser. No. 09/633,753, and which is incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60325767 |
Aug 2000 |
US |