Dimethyl Sulfoxide → HCID 136403363, compound

HRID 1534965Notes

Reaction equation

HRID 1534965 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.[CH3:25][NH:26][CH2:27][C@H:28]([OH:37])[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([OH:36])[CH:30]=1.CS(C)=O>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]([N:26]([CH2:27][CH:28]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([OH:36])[CH:30]=3)[OH:37])[CH3:25])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5816Epinephrine2×HCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 136403363HCID 136403363, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 0.167 g (0.9111 mmol) of (R)-(-)-epinephrine were placed into a 10 ml round bottom flask with 2 ml dimethylsulfoxide (dried over barium oxide) and a magnetic stirring bar. The solution was stirred at room temperature (25°) and was initially heterogeneous. After about 45 minutes, as the epinephrine began to react with AIT-0081, the solution was a nearly homogeneous yellow orange color. The solution was stirred an additional two hours, drawn into a pasteur pipet, and added with stirring to a flask containing 50 ml acetone and a magnetic stirring bar. A copious white precipitate formed and the solution was stirred for ten minutes. The solution was filtered by vacuum and the white solid washed with acetone. The Buchner funnel was immediately placed under high vacuum to remove small traces of dimethylsulfoxide. 120 mg of a white solid, 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-N-methylpropanamide (AIT-0100), was obtained. Yield: 48%.

Workup

  1. customto react with AIT-0081
  2. stirringThe solution was stirred an additional two hours
  3. additionadded
  4. stirringwith stirring to a flask
  5. customA copious white precipitate formed
  6. stirringthe solution was stirred for ten minutes
  7. filtrationThe solution was filtered by vacuum
  8. washthe white solid washed with acetone
  9. customto remove small traces of dimethylsulfoxide

Sources & evidence

ORD record
ord-a5ebcea5d75b40388e32670f64c01b4c
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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