Dimethyl Sulfoxide → 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]butanoic acid, methyl ester
Reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.Cl.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31].CS(C)=O.C(N(CC)CC)C>CC(C)=O>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:15])[CH:5]=[N:4][C:3]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) and 0.142 g (0.925 mmol) of gamma amino butyric acid, methyl ester hydrochloride were placed into a 10 ml round bottom flask with a magnetic stirring bar and 2 ml dimethylsulfoxide. To this solution was added 0.100 g (0.988 mmol) of triethylamine. The solution immediately turned green and was stirred at room temperature for one hour. Then 5 ml of acetone was added and the solution was filtered. The mother liquor was treated with ether (approximately 35 ml) to precipitate the product. Upon filtration and washing with ether, 232 mg of a white solid 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]butanoic acid, methyl ester (AIT-0092) was obtained. Yield: 83%.
Workup
- filtrationthe solution was filtered
- additionThe mother liquor was treated with ether (approximately 35 ml)
- customto precipitate the product
- filtrationUpon filtration
- washwashing with ether
Sources & evidence
- ORD record
- ord-cab939ba634247a2b194ab0ec3f8e44d
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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