Acetic Anhydride → HCID 16122493, compound

HRID 1369024Notes

Reaction equation

HRID 1369024 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]1([CH3:28])[CH2:22][O:23][C:24]([CH3:27])([CH3:26])[O:25][C@@H:5]1[CH2:4][CH2:3]2.[C:29](OC(=O)C)(=[O:31])[CH3:30]>O>[CH3:30][C:29]([O:21][C@@H:16]1[CH2:17][O:18][C:19](/[C:15]/1=[CH:14]/[CH2:13][C@H:12]1[C@:2]2([CH3:1])[CH2:3][CH2:4][C@H:5]3[O:25][C:24]([CH3:27])([CH3:26])[O:23][CH2:22][C@@:6]3([CH3:28])[C@H:7]2[CH2:8][CH2:9][C:10]1=[CH2:11])=[O:20])=[O:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 16122395HCID 16122395, compound

Product 1

HCID 16122493HCID 16122493, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,19-Isopropylidene andrographolide (15 g) obtained in step 1 was refluxed in distilled acetic anhydride (110 ml) for 45 min. After confirming the complete formation of the product (by TLC analysis), the contents were cooled to room temperature, diluted with water (500 ml) and extracted with dichloromethane (3×200 ml). The organic layer was separated and dried over Na2SO4 and concentrated to get a brown oily material. The crude material was purified by flash column chromatography (silica gel 230-400 mesh; 250 g, eluting system light petrol: ethyl acetate=85:15) to obtain pure 14-acetyl-3,19-isopropylidene andrographolide (13 g).

Workup

  1. extractionextracted with dichloromethane (3×200 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto get a brown oily material
  6. customThe crude material was purified by flash column chromatography (silica gel 230-400 mesh; 250 g, eluting system light petrol: ethyl acetate=85:15)

Sources & evidence

ORD record
ord-0a493d40225a4fa8844055e2a0a1c027
Source dataset
uspto-grants-2003_06
Patent number
US06576662B2

Reaction notes

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