Ammonia → (+/-)-3-(2-Furanyl)-4,5-dihydro-1-(3-mercapto-1-oxopropyl)-1H-pyrazole-5-carboxylic acid
Reaction equation
N.C([S:5][CH2:6][CH2:7][C:8]([N:10]1[CH:14]([C:15]([OH:17])=[O:16])[CH2:13][C:12]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[N:11]1)=[O:9])(=O)C>>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[C:12]1[CH2:13][CH:14]([C:15]([OH:17])=[O:16])[N:10]([C:8](=[O:9])[CH2:7][CH2:6][SH:5])[N:11]=1Participants
Procedure
Aqueous ammonia (12 cc) is stirred under nitrogen at 10° C. for 30 minutes, at which point 4.3 g of (±)-1-[3-(acetylthio)-1-oxopropyl]-3-(2-furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid is added. The resulting solution is stirred for about 2.5 hours under nitrogen. The solution is extracted with ethyl acetate (discarded) and then made strongly acid with 20% HCl. An oil results which is extracted with 150 cc ethyl acetate. The aqueous layer is extracted with an additional two 150 cc portions of ethyl acetate. The combined organic layers are extracted with 200 cc saturated NaCl and then dried over MgSO4. The solvent is removed to yield 3.7 g of semicrystalline residue which is triturated with ether to yield 2.3 g of product melting at 121°-123° C. The product does not crystallize readily from any solvent tried.
Workup
- additionis added
- extractionThe solution is extracted with ethyl acetate (discarded)
- customAn oil results which
- extractionis extracted with 150 cc ethyl acetate
- extractionThe aqueous layer is extracted with an additional two 150 cc portions of ethyl acetate
- extractionThe combined organic layers are extracted with 200 cc saturated NaCl
- dry with materialdried over MgSO4
- customThe solvent is removed
- customto yield 3.7 g of semicrystalline residue which
- customis triturated with ether
Sources & evidence
- ORD record
- ord-3bfd29346e5e43a683483e7a35f920ef
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254267
Reaction notes
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