Benzyl Chloride → Benzyl ursolate

HRID 1402656Notes

Reaction equation

HRID 1402656 reaction equation
[CH3:1][C@H:2]1[C@H:28]([CH3:29])[C@@H:27]2[C@@:5]([C:31]([OH:33])=[O:32])([CH2:6][CH2:7][C@@:8]3([CH3:30])[C@:13]4([CH3:26])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[CH2:19][CH2:18][C@:17]5([CH3:25])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH2:41](Cl)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C)C=O>[CH3:1][C@H:2]1[C@H:28]([CH3:29])[C@@H:27]2[C@@:5]([C:31]([O:33][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:32])([CH2:6][CH2:7][C@@:8]3([CH3:30])[C@:13]4([CH3:26])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[CH2:19][CH2:18][C@:17]5([CH3:25])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 64945(+)-Ursolic Acid

Product 1

HCID 67952979Benzyl ursolate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5 g of ursolic acid was dissolved in 300 ml of dimethylformamide, and 63 ml of triethylamine was added thereto. Then, 20 g of benzyl chloride was added thereto, and the whole was stirred at 50° C. for 1 hour and concentrated under reduced pressure, followed by purification by silica gel chromatography (elution solvent; chloroform:methanol=100:0 to 80:20), to thereby obtain benzyl ursolate.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customfollowed by purification by silica gel chromatography (elution solvent; chloroform:methanol=100:0 to 80:20)

Sources & evidence

ORD record
ord-604734b8b5fd46e0ac64648fe2e785ff
Source dataset
uspto-grants-2014_12
Patent number
US08912172B2

Reaction notes

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