Protease inhibitor precursor synthesis
View Patent ↗The present invention provides a compound having the structure (I) and processes for the production thereof and the intermediates used in such process.
1. A compound having the formula (II) or a stereoisomer thereof,
wherein
X and Y are independently selected from Si and C; and,
R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of —H and monovalent hydrocarbon radicals;
R 1 and R 2 can be taken together to form a bivalent hydrocarbon radical represented by —R 1 -R 2 —;
R 3 and R 4 can be taken together to form a bivalent hydrocarbon radical represented by —R 3 -R 4 —;
or a salt form thereof.
2. A compound according to claim 1 wherein the compound is one of the following stereoisomers
3. A process for the production of a compound as described in claim 1 comprising oxidizing a compound having the formula (III)
wherein
X and Y are independently selected from Si and C; and,
R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of —H and monovalent hydrocarbon radicals;
R 1 and R 2 can be taken together to form a bivalent hydrocarbon radical represented by —R 1 -R 2 —;
R 3 and R 4 can be taken together to form a bivalent hydrocarbon radical represented by —R 3 -R 4 —;
to obtain a compound of formula (II).
4. A compound according to claim 1 , wherein X and Y are the same and are C.
5. A compound according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of —H, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkoxyalkyl, C 7-20 alkoxyaryl, C 2-20 alkynyl, C 3-30 cycloalkyl, C 4-30 (cycloalkyl)alkyl, C 4-30 (cycloalkenyl)alkyl, C 9-30 (cycloalkynyl)alkyl, C 3-30 cycloalkenyl, C 4-30 cycloalkynyl, C 7-30 arylalkyl, C 7-30 alkylaryl, C 6-30 aryl, C 6-30 heterocyclylalkyl, C 6-30 alkylheterocyclyl and C 5-3 heterocyclyl.
6. A compound according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of —H, primary or secondary C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkoxyC 1-6 alkyl, C 1-6 alkoxyC 5-10 aryl, C 5-7 cycloalkyl, C 5-11 cycloalkylC 1-6 alkyl, C 4-11 cycloalkenylC 1-6 alkyl, C 8-12 cycloalkynylC 1-6 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkynyl, C 6-11 arylC 1-6 alkyl, C 1-6 alkylC 6-11 aryl, C 6-11 aryl, C 5-12 heterocyclylC 1-6 alkyl, C 1-6 alkylC 5-12 heterocyclyl and C 5-12 heterocyclyl.
7. A compound according to claim 1 , wherein R 1 , R 2 , R 3 and R 4 are the same.
8. A compound according to claim 1 , wherein X and Y are C and R 1 , R 2 , R 3 and R 4 are the same and are selected from the group consisting of methyl, ethyl, n-propyl, s-propyl, n-butyl, s-butyl, t-butyl, benzyl, phenyl and methoxyphenyl.
9. A process for the production of a compound as described in claim 2 comprising oxidizing a compound having the formula (III)
wherein
X and Y are independently selected from Si and C; and,
R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of —H and monovalent hydrocarbon radicals;
R 1 and R 2 can be taken together to form a bivalent hydrocarbon radical represented by —R 1 -R 2 —;
R 3 and R 4 can be taken together to form a bivalent hydrocarbon radical represented by —R 3 -R 4 —;
to obtain a compound of formula (II).
10. A process according to claim 3 , wherein the oxidation is carried out using Swern, Pfitzner-Moffatt or Parikh-Doering conditions.