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US 9,790,223 B2Granted
Process for preparation of sodium (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate
AssigneeWockhardt Limited
InventorsVijay Prakash Chavan, Karuna Suresh Wankhede, Vikas Vithalrao Deshmukh, Satish Bhavsar, Kiran Ramchandra Patil, Ravindra Dattatraya Yeole, Prasad Keshav Deshpande, Mahesh Vithalbhai Patel
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Abstract
A process for preparation of a compound of Formula (I) is disclosed.
Claims10
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 P1 is H or an amine protecting group and P2 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 P1 and P2 are as defined above;
- (c) cyclizing a compound of Formula (IV) to obtain a compound of Formula (V);
- wherein P1 and P2 are as defined above;
- (d) reducing a compound of Formula (V) to obtain a compound of Formula (VI);
- wherein P1 and P2 are as defined above;
- (e) converting a compound of Formula (VI) to a compound of Formula (VII);
- wherein P2 is as defined above;
- (f) cyclizing a compound of Formula (VII) to obtain a compound of Formula (VIII), optionally followed by diastereomeric separation;
- wherein P2 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).
13 more elements
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 P1 is tert-butyloxycarbonyl and P2 is tert-butyldimethylsilyl;
- (b) reacting a compound of Formula (III) with O-benzyl hydroxylamine hydrochloride to obtain a compound of Formula (IV);
- wherein P1 and P2 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 P1 and P2 are as defined above;
- (d) reducing a compound of Formula (V) in presence of sodium cyanoborohydride to obtain a compound of Formula (VI);
- wherein P1 and P2 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 P2 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 P2 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).
13 more elements
Dependencies are inferred from the claim text.