Triptolide → HCID 49835973, compound

HRID 2220363Notes

Reaction equation

HRID 2220363 reaction equation
[CH3:1][CH:2]([C@@:4]12[C@@H:19](O)[C@:18]34[O:21][C@H:17]3[CH2:16][C@@H:15]3[C@:10]([CH3:26])([CH2:11][CH2:12][C:13]5[C:24](=[O:25])[O:23][CH2:22][C:14]=53)[C@:8]34[O:9][C@H:7]3[C@@H:5]1[O:6]2)[CH3:3].C(N(S(F)(F)[F:33])CC)C.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][CH:2]([C@@:4]12[C@H:19]([F:33])[C@:18]34[O:21][C@H:17]3[CH2:16][C@@H:15]3[C@:10]([CH3:26])([CH2:11][CH2:12][C:13]5[C:24](=[O:25])[O:23][CH2:22][C:14]=53)[C@:8]34[O:9][C@H:7]3[C@@H:5]1[O:6]2)[CH3:3]

Participants

5

Reactant 3

HCID 107985TriptolideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 49835973HCID 49835973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of PG490 (triptolide, 17.3 mg, 0.048 mmol) in dichloromethane (1.0 ml) at 0° C. was added (diethylamino)sulfur trifluoride (DAST, 100 μl, 0.763 mmol) under N2. The reaction mixture was stirred at 0° C. for 2 hrs, and saturated NaHCO3 solution (0.8 ml) was then added. The reaction mixture was extracted with 3×2 ml of dichloromethane. The combined organic layer was dried over anhydrous NaSO4 and concentrated under vacuum. The desired product (PG763) was obtained in quantitative yield.

Workup

  1. extractionThe reaction mixture was extracted with 3×2 ml of dichloromethane
  2. dry with materialThe combined organic layer was dried over anhydrous NaSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9b33ddf1fdf440dd81d3e55b6dca44f0
Source dataset
uspto-grants-2008_08
Patent number
US07417069B2

Reaction notes

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