Asiatic Acid → HCID 21672634, compound

HRID 1420518Notes

Reaction equation

HRID 1420518 reaction equation
[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([OH:35])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@@:21]([CH2:23][OH:24])([CH3:22])[C@@H:20]([OH:25])[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.[N+](=[CH2:38])=[N-].CCOCC>CO>[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([O:35][CH3:38])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@@:21]([CH2:23][OH:24])([CH3:22])[C@@H:20]([OH:25])[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 119034Asiatic AcidHCID 21186548Diazomethane diethylether

Product 1

HCID 21672634HCID 21672634, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Asiatic acid (500 mg) was dissolved in methanol (25 ml), and the solution was cooled to 0° C. An excess amount of diazomethane/ether solution was added, and the resultant mixture was stirred at room temperature for 1 hour. The solvent was removed by evaporation under reduced pressure, and the residue was purified by column chromatography (eluent: dichloromethane/methanol=30:1) to give 490 mg of white solid(yield: 95%). The product was recrystallized from ethyl acetate to obtain needle-like crystals.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography (eluent: dichloromethane/methanol=30:1)

Sources & evidence

ORD record
ord-50fad53cc59340b8b3d787d5c9660f73
Source dataset
uspto-grants-2000_06
Patent number
US06071898

Reaction notes

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