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, 67.9 mmol) was stirred vigorously in 200 mL of 1N sodium hydroxide solution for 1 hour. The mixture was then extracted twice with 100 mL of diethyl ether, 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 ingredients 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 purification.
Workup
- extractionThe mixture was then extracted twice with 100 mL of 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 purification
Sources & evidence
- ORD record
- ord-9832b58a18594b9a85fca5add5a83dab
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937073B2
Reaction notes
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