Process for the synthesis of HIV protease inhibitors
AssigneeGlaxo Wellcome Inc.
InventorsEmile Al-Farhan, David D. Deininger, Stephen McGhie, John O'Callaghan, Mark Stuart Robertson, Keith Rodgers, Stephen John Rout, Hardew Singh, Roger Dennis Tung
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Abstract
An improved process for the synthesis of (3S)-tetrahydro-3-furyl N-[(1S,2R)-3 -(4-amino-N-isobutylbenzenesulphonamido)-1-benzyl-2-hydroxypropyl]carbamate comprising four steps form the compound of formula A and a novel intermediate thereto.
Claims12
A process for the preparation of the compound of formula (I)
- comprising:
- i) reacting a p-nitrophenylsulfonyl group with a compound of formula (A)
- in which P is an amine-protecting group;
- ii) deprotecting the resultant compound of step i);
- iii) reacting the resultant compound of step (ii) with a tetrahydrofuryloxy carbonyl group;
- or reacting the resultant compound of step ii) with phosgene, or equivalent, and reacting the resultant intermediate with (S)-tetrahydro-3-furanol;
- and
- iv) reducing the resultant compound of step iii) to form a compound of formula (I).
A process as claimed in any preceding claim in which step ii) is carried out in ethanol or toluene.
The compound (2R,3S)-N-(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzene sulphonamide hydrochloride and solvates thereof.
Dependencies are inferred from the claim text.