Reaction equation
[CH3:1][C@:2]12[C@H:12]([CH2:13]/[CH:14]=[C:15]3\[C@H:16]([OH:21])[CH2:17][O:18][C:19]\3=[O:20])[C:10](=[CH2:11])[CH2:9][CH2:8][C@@H:7]1[C@@:6]([CH2:23][OH:24])([CH3:22])[C@H:5]([OH:25])[CH2:4][CH2:3]2.[C:26]1(C)[CH:31]=CC(S([O-])(=O)=O)=C[CH:27]=1.[NH+]1C=CC=CC=1.C1(C)C=CC=CC=1.CS(C)=O>COC(OC)(C)C>[CH3:1][C@:2]12[C@H:12]([CH2:13]/[CH:14]=[C:15]3\[C@H:16]([OH:21])[CH2:17][O:18][C:19]\3=[O:20])[C:10](=[CH2:11])[CH2:9][CH2:8][C@@H:7]1[C@:6]1([CH3:22])[CH2:23][O:24][C:26]([CH3:31])([CH3:27])[O:25][C@@H:5]1[CH2:4][CH2:3]2Participants
5
Conditions
- Temperature
- 80 °C
Procedure
Andrographolide (150 mg, 0.43 mmol) was dissolved in a mixture solution of 2,2-dimethoxypropane (0.2 mL), pyridinium p-toluene-sulfonate (3 mg) and toluene/DMSO (3 mL/0.4 mL), stirred at 80° C. for 1 hour, and cooled to room temperature at the end. The reaction was terminated by using triethylamine (0.1 mL), the reaction mixture was diluted with toluene (20 mL), washed with water (3×5 mL), the organic layer was dried using anhydrous Na2SO4 and concentrated, and the obtained white solid was washed with ethyl ether and filtrated to obtain the compound 1 (130 mg, 78%) (Srinivas et al., Bioorg. Med. Chem. Lett. 2004, 14, 4711-4717).
Workup
- temperaturecooled to room temperature at the end
- customThe reaction was terminated
- additionthe reaction mixture was diluted with toluene (20 mL)
- washwashed with water (3×5 mL)
- customthe organic layer was dried
- concentrationconcentrated
- washthe obtained white solid was washed with ethyl ether
- filtrationfiltrated
Sources & evidence
- ORD record
- ord-8b4b80bd476f494ea0edaec42d30e49b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367720B2
Linked notes
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