Sodium Acetate → Scillarenin

HRID 2367945Notes

Reaction equation

HRID 2367945 reaction equation
C[C@@H]1O[C@@H]([O:8][C@@H:9]2[CH:25]=[C:24]3[C@@:12]([CH3:35])([C@@H:13]4[C@@H:21]([CH2:22][CH2:23]3)[C@:20]3([OH:26])[C@@:16]([CH3:34])([C@@H:17]([C:27]5[CH:33]=[CH:32][C:30](=[O:31])[O:29][CH:28]=5)[CH2:18][CH2:19]3)[CH2:15][CH2:14]4)[CH2:11][CH2:10]2)[C@H](O)[C@H](O)[C@H]1O.C([O-])(=O)C.[Na+]>C(O)C>[CH3:35][C@@:12]12[C@H:13]3[CH2:14][CH2:15][C@:16]4([CH3:34])[C@@H:17]([C:27]5[CH:33]=[CH:32][C:30](=[O:31])[O:29][CH:28]=5)[CH2:18][CH2:19][C@:20]4([OH:26])[C@@H:21]3[CH2:22][CH2:23][C:24]1=[CH:25][C@@H:9]([OH:8])[CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 5284613Proscillaridin

Product 1

HCID 12315393ScillareninYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Proscillaridin (3 g, 5.6 mmol) was dissolved in ethanol (57 ml) at 40° C. while stirring, to this solution was added 171 ml of sodium acetate buffer (pH=4, 0.02 M) at 40° C., followed by naringinase (1.03 g). The reaction was stirred for 24 hours, when ethanol was added (200 ml) and the solvent was removed in vacuo, an additional 100 ml ethanol was added and the solvent was removed in vacuo. Material was purified by flash chromatography (DCM to 9:1 DCM:MeOH) to give 9 as an off-white solid (1.9 g, 4.9 mmol, 90%). 1H-NMR (CDCl3, 300 MHz): 7.89 (dd, J=9.7, 2.6 Hz, 1H), 7.26 (dd, J=2.6, 0.9 Hz, 1H), 6.27 (dd, J=9.7, 0.9, 1H), 5.31 (s, 1H), 4.31 (m, 1H), 2.47 (dd, J=9.3, 6.2 Hz, 1H), 2.25-0.98 (m, 19H), 1.04 (s, 3H), 0.73 (s, 3H) 13C-NMR (CDC13, 75 MHz): 163.28, 148.77, 147.59, 146.42, 123.90, 123.35, 115.22, 85.01, 67.65, 51.20, 50.38, 48.46, 42.65, 40.82, 37.58, 35.71, 32.65, 32.36, 29.17, 28.89, 28.76, 21.43, 19.10, 16.69.

Workup

  1. stirringThe reaction was stirred for 24 hours
  2. customthe solvent was removed in vacuo
  3. additionan additional 100 ml ethanol was added
  4. customthe solvent was removed in vacuo
  5. customMaterial was purified by flash chromatography (DCM to 9:1 DCM:MeOH)

Sources & evidence

ORD record
ord-c186d49a4df740848bbe078ff1dbd0e3
Source dataset
uspto-grants-2014_04
Patent number
US08703723B2

Reaction notes

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