n-Butyl(S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylate → (S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid
Reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]([NH:10][C@@:11]2([C:16]([O:18]CCCC)=[O:17])[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])=[CH:3]1>[OH-].[Na+]>[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]([NH:10][C@@:11]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14][O:13][CH2:12]2)=[O:9])=[CH:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
n-Butyl (S)-3-[(6-oxo-1,6-dihydro-pyridazine-4-carbonyl)-amino]-tetrahydrofuran-3-carboxylate (21.0 g) was stirred in 200 mL of 1N sodium hydroxide solution for 1 hour. The mixture was then extracted twice with 100 mL diethyl ether, and the alkaline aqueous phase was then combined with 50 mL of 4N hydrochloric acid. The mixture was then evaporated to dryness and the residue was stirred with 150 mL ethanol. Undissolved constituents were then filtered off and the filtrate was evaporated down. In this way the product was obtained in a yield of 71% of theory. The product thus obtained was further processed without any further purification.
Workup
- extractionThe mixture was then extracted twice with 100 mL diethyl ether
- customThe mixture was then evaporated to dryness
- filtrationwere then filtered off
- customthe filtrate was evaporated down
- customIn this way the product was obtained in a yield of 71% of theory
- customThe product thus obtained
- customwas further processed without any further purification
Sources & evidence
- ORD record
- ord-48e0b40b6b0741b5a2aa383f1e3f40de
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901127B2
Reaction notes
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