Process for the preparation of vitamin k2
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.
Claims
exact text as granted — not AI-modified1 - 9 . (canceled)
10 . A compound
wherein R is an alkyl group.
11 . The compound as claimed in claim 10 of formula
12 . A process for the preparation of MK-7 comprising converting a compound
wherein R is an alkyl group into MK-7:
13 . The process as claimed in claim 12 wherein conversion is achieved using cerium ammonium nitrate.
14 . 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 —SO 2 Ar to hydrogen to give diprotected naphthoquinone:
and
(iii) converting the diprotected naphthoquinone into a naphthoquinone ring.
15 . The process as claimed in claim 14 wherein the deprotonation step (i) is achieved using BuLi.
16 . The process as claimed in claim 14 wherein Ar is Ph.
17 . The process as claimed in claim 14 wherein LG is a halide.
18 . The process as claimed in claim 14 wherein the step (iii) reduction uses cerium ammonium nitrate.
19 . The process as described in claim 14 wherein the compound of formula (I) is MK-7.
20 . 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 —SO 2 Ar to hydrogen to give diprotected naphthoquinone:
and
(iii) converting the diprotected naphthoquinone into a naphthoquinone ring.
21 . 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 —SO 2 Ar to hydrogen and
(iii) converting the diprotected naphthoquinone into a naphthoquinone ring.
22 . 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 —SO 2 Ar groups to hydrogen to form diprotected naphthoquinone
and
(iii) converting the diprotected naphthoquinone into a naphthoquinone ring.Cited by (0)
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