Dimethyl Sulfoxide → 3-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]propane sulfonic acid
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.[NH2:25][CH2:26][CH2:27][CH2:28][S:29]([OH:32])(=[O:31])=[O:30].CS(C)=O.C(N(CC)CC)C>CCOCC.CO.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:25][CH2:26][CH2:27][CH2:28][S:29]([OH:32])(=[O:31])=[O:30])=[O:15])[CH:5]=[N:4][C:3]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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 0.127 g (0.9111 mmol) of 3-amino-1-propane sulfonic acid were placed into a 10 ml round bottom flask with 2 ml of dimethylsulfoxide and a magnetic stirring bar. To this solution was added 0.100 g (0.988 mmol) of triethylamine and the solution immediately turned green. The solution was stirred at room temperature for five hours. Dimethylsulfoxide was removed in vacuo with gentle heating. 9 ml of acetone was added and the solution was triturated with methanol until homogeneous. No precipitate had formed. The solution was transferred to a 50 ml round bottom flask with 10 ml acetone and 5 ml methanol. Ether was added until just before the cloud point and the flask was placed into freezer overnight (<0° C.).
Workup
- customDimethylsulfoxide was removed in vacuo with gentle heating
- addition9 ml of acetone was added
- customthe solution was triturated with methanol until homogeneous
- customNo precipitate had formed
- waitthe flask was placed into freezer overnight
- custom(<0° C.)
Sources & evidence
- ORD record
- ord-0d228c4559ca42bc801ef017038cdcff
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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