Benzoic Acid → Sarsasapogenin benzoate

HRID 2238460Notes

Reaction equation

HRID 2238460 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:15][C@H:16]1[CH2:44][O:43][C@@:19]2([O:23][C@H:22]3[CH2:24][C@H:25]4[C@@H:30]5[CH2:31][CH2:32][C@@H:33]6[CH2:38][C@H:37]([OH:39])[CH2:36][CH2:35][C@:34]6([CH3:40])[C@H:29]5[CH2:28][CH2:27][C@:26]4([CH3:41])[C@H:21]3[C@@H:20]2[CH3:42])[CH2:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:64](O)(=[O:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>C1COCC1>[CH3:15][CH:16]1[CH2:44][O:43][C:19]2([O:23][CH:22]3[CH2:24][CH:25]4[CH:30]5[CH2:31][CH2:32][CH:33]6[CH2:38][CH:37]([O:39][C:64]([C:65]7[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=7)=[O:71])[CH2:36][CH2:35][C:34]6([CH3:40])[CH:29]5[CH2:28][CH2:27][C:26]4([CH3:41])[CH:21]3[CH:20]2[CH3:42])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 99512EpismilageninHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 587040Sarsasapogenin benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisopropylazodicarboxylate (0.81 g, 4.0 mmol) in dry THF (2 ml) was added to a stirred solution of epismilagenin (0.83 g, 2.0 mmol), triphenylphosphine (1.05 g, 4.0 mmol) and benzoic acid (0.49 g, 4.0 mmol) in dry THF (20 ml). The mixture was stirred at room temperature and monitored by TLC. After 2 h all the starting material had been consumed. The solvent was removed in vacuo, the residual syrup dissolved in ether (30 ml) and the solution washed with aqueous saturated sodium hydrogen carbonate (25 ml). The organic layer was dried over MgSO4 and passed down a short silica pad, the pad being washed with ether. The combined washings and filtrate were concentrated in vacuo to afford smilagenin benzoate as a white solid.

Workup

  1. customAfter 2 h all the starting material had been consumed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residual syrup dissolved in ether (30 ml)
  4. washthe solution washed with aqueous saturated sodium hydrogen carbonate (25 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. washthe pad being washed with ether
  7. concentrationThe combined washings and filtrate were concentrated in vacuo

Sources & evidence

ORD record
ord-81d18ed4540d494aa2d965d267e8f063
Source dataset
uspto-grants-2010_05
Patent number
US07718792B2

Reaction notes

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