Sodium Bicarbonate → 7beta-Acetoxy-3-hydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

HRID 28341Notes

Reaction equation

HRID 28341 reaction equation
C([O:4][C:5]1[C:22]([I:23])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]4)[C@@H:9]([O:25][C:26](=[O:28])[CH3:27])[CH2:8][C:7]=2[CH:6]=1)(=O)C.C(=O)(O)[O-].[Na+]>CO>[C:26]([O:25][C@H:9]1[CH2:8][C:7]2[CH:6]=[C:5]([OH:4])[C:22]([I:23])=[CH:21][C:20]=2[C@@H:19]2[C@@H:10]1[C@H:11]1[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 691050063,7beta-Diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one

Product 1

HCID 116696607beta-Acetoxy-3-hydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (1.4 mmol) of 3,7β-diacetoxy-2-iodo-estra-1,3,5(10)-trien-17-one was dissolved in 30 ml of methanol, mixed with 1.0 g of sodium bicarbonate, and the reaction mixture was stirred overnight. Then, it was filtered, and the solution was concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate) yielded 402 mg (63%) of colorless crytstals.

Workup

  1. filtrationThen, it was filtered
  2. concentrationthe solution was concentrated by evaporation in a rotary evaporator
  3. customFlash chromatography (cyclohexane/ethyl acetate) yielded 402 mg (63%) of colorless crytstals

Sources & evidence

ORD record
ord-022b672239c24da4b4aa20a12dc2b233
Source dataset
uspto-grants-2008_09
Patent number
US07419972B2

Reaction notes

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