Process for the preparation of vitamin k2
AssigneeKappa Bioscience AS
InventorsLars SKATTEBOL, Inger Reidun AUKRUST, Marcel SANDBERG
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Abstract
Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I) is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III) wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.
Claims10
1-9. (canceled)
A process for the preparation of MK-7 comprising converting a compound
- wherein R is an alkyl group;
- into MK-7:
- wherein conversion is achieved using cerium ammonium nitrate.
A process for the preparation of a compound of formula (I)
- wherein n is 1 to 9;
- comprising (i) deprotonating alpha to the sulphur a compound of formula:
- wherein R is an alkyl group;
- and
- Ar is an aryl group such as phenyl;
- and reacting with a compound of formula
- wherein m is 0 to 8;
- and
- LG is a leaving group;
- to obtain
- (ii) reducing the SAr or —SO2Ar to hydrogen to give diprotected naphthoquinone:
- and
- (iii) converting the diprotected naphthoquinone into a naphthoquinone ring;
- wherein the step (iii) reduction uses cerium ammonium nitrate.
A process for the preparation of a compound of formula (I)
- comprising (i) deprotonating alpha to the sulphur a compound of formula
- wherein R is an alkyl group;
- and
- Ar is an aryl group such as phenyl;
- and reacting with a compound of formula
- wherein m is 4;
- and
- LG is a leaving group;
- to obtain
- (ii) reducing the SAr or —SO2Ar to hydrogen to give diprotected naphthoquinone:
- and
- (iii) converting the diprotected naphthoquinone into a naphthoquinone ring wherein the step (iii) reduction uses cerium ammonium nitrate.
A process for the preparation of a compound of formula (I)
- comprising deprotonating alpha to the sulphur a compound of formula
- wherein R is an alkyl group;
- and
- Ar is an aryl group such as phenyl;
- and reacting with a compound of formula
- wherein LG is a leaving group;
- to obtain
- (ii) reducing the SAr or —SO2Ar to hydrogen and
- (iii) converting the diprotected naphthoquinone into a naphthoquinone ring wherein the step (iii) reduction uses cerium ammonium nitrate.
A process for the preparation of a compound of formula (I)
- comprising deprotonating alpha to the sulphur a compound of formula
- wherein R is an alkyl group;
- and
- Ar is an aryl group such as phenyl;
- and reacting with a compound of formula
- wherein LG is a leaving group;
- to obtain
- (ii) reducing the SAr or —SO2Ar groups to hydrogen to form diprotected naphthoquinone
- and
- (iii) converting the diprotected naphthoquinone into a naphthoquinone ring wherein the step (iii) reduction uses cerium ammonium nitrate.
Dependencies are inferred from the claim text.