Process for preparation of sodium (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Patent metadata

Field	Value
Publication number	US-9790223-B2
Application number	US-201515125554-A
Country	US
Kind code	B2
Filing date	Mar 12, 2015
Priority date	Mar 14, 2014
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

A process for preparation of a compound of Formula (I) is disclosed.

First claim

The invention claimed is:

1. A process for preparation of a compound of Formula (I),

said process comprising:
(a) reacting a compound of Formula (II) with trimethylsulfoxonium iodide to obtain a compound of Formula (III); wherein P 1 is H or an amine protecting group and P 2 is H or an alcohol protecting group;

(b) reacting a compound of Formula (III) with O-benzyl hydroxylamine hydrochloride to obtain a compound of Formula (IV); wherein P 1 and P 2 are as defined above;

(c) cyclizing a compound of Formula (IV) to obtain a compound of Formula (V); wherein P 1 and P 2 are as defined above;

(d) reducing a compound of Formula (V) to obtain a compound of Formula (VI); wherein P 1 and P 2 are as defined above;

(e) converting a compound of Formula (VI) to a compound of Formula (VII); wherein P 2 is as defined above;

(f) cyclizing a compound of Formula (VII) to obtain a compound of Formula (VIII), optionally followed by diastereomeric separation; wherein P 2 is as defined above;

(g) deprotecting a compound of Formula (VIII) to obtain a compound of Formula (IX); and

(h) oxidizing a compound of Formula (IX), followed by sodium salt formation to obtain a compound of Formula (I).

2. The process according to claim 1 , wherein the P 1 is tert-butoxycarbonyl and P 2 is tert-butyldimethylsilyl.

3. The process according to claim 1 , wherein a compound of Formula (V) is obtained by cyclizing a compound of Formula (IV) in presence of a base selected from a group consisting of sodium hydride, potassium tert-butoxide and n-butyl lithium.

4. The process according to claim 1 , wherein a compound of Formula (VI) is obtained by reducing a compound of Formula (V) in presence of a reducing agent selected from a group consisting of sodium borohyride, sodium cyanoborohydride, sodium triacetoxyborohydride, sodium tripropanoyloxyborohydride and lithium borohydride.

5. The process according to claim 1 , wherein a compound of Formula (VII) is obtained by treating a compound of Formula (VI) with a deprotecting agent selected from a group consisting of hydrochloric acid, trifluoroacetic acid, hydrobromic acid, sulphuric acid, boron trifluoride etherate complex, piperidine, ammonia, methylamine, ammonium cerium (IV) nitrate and hydrogen source in presence of a transition metal catalyst.

6. The process according to claim 1 , wherein a compound of Formula (VIII) is obtained by cyclizing a compound of Formula (VII) in presence of a reagent selected from the group consisting of triphosogene, phosgene or carbonyldiimidazole.

7. The process according to claim 1 , wherein the diastereomeric separation of compound of Formula (VIII) is obtained by carrying out crystallization in a solvent selected from a group consisting of n-hexane, cyclohexane, heptanes, methyl alcohol, ethyl alcohol, isopropyl alcohol, water or a mixture thereof.

8. The process according to claim 1 , wherein sodium salt formation in step (h) is carried out in presence of sodium-2-ethyl hexanoate.

9. A process for preparation of a compound of Formula (I),

said process comprising:
(a) reacting a compound of Formula (II) with trimethylsulfoxonium iodide to obtain a compound of Formula (III); wherein P 1 is tert-butyloxycarbonyl and P 2 is tert-butyldimethylsilyl;

(b) reacting a compound of Formula (III) with O-benzyl hydroxylamine hydrochloride to obtain a compound of Formula (IV); wherein P 1 and P 2 are as defined above;

(c) cyclizing a compound of Formula (IV) in presence of potassium tert-butoxide to obtain a compound of Formula (V); wherein P 1 and P 2 are as defined above;

(d) reducing a compound of Formula (V) in presence of sodium cyanoborohydride to obtain a compound of Formula (VI); wherein P 1 and P 2 are as defined above;

(e) deprotecting a compound of Formula (VI) in presence of boron trifluoride etherate complex to obtain a compound of Formula (VII); wherein P 2 is as defined above;

(f) cyclizing a compound of Formula (VII) in presence of triphosgene to obtain a compound of Formula (VIII), optionally followed by diastereomeric separation; wherein P 2 is as defined above;

(g) deprotecting a compound of Formula (VIII) in presence of tetra n-butylammonium fluoride to obtain a compound of Formula (IX); and

(h) oxidizing a compound of Formula (IX), followed by sodium salt formation to obtain a compound of Formula (I).

10. The compound of Formula (VIII) according to claim 9 , wherein P 2 is tert-butyldimethylsilyl, having diastereomeric purity of at least 99% as determined by HPLC

Assignees

• Wockhardt Ltd

Inventors

• Chavan Vijay Prakash
• Wankhede Karuna Suresh
• Deshmukh Vikas Vithalrao
• Bhavsar Satish
• Patil Kiran Ramchandra
• Yeole Ravindra Dattatraya
• Deshpande Prasad Keshav
• Patel Mahesh Vithalbhai

Classifications

• C07D471/08 Primary

  Bridged systems · CPC title

• C07C251/36

  with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07D211/56 Primary

  Nitrogen atoms (nitro radicals C07D211/38) · CPC title

• C07C249/08

  by reaction of hydroxylamines with carbonyl compounds · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title