Sodium Chloride → HCID 66846001, compound

HRID 876208Notes

Reaction equation

HRID 876208 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21].C(OC(N=NC(OC(C)C)=O)=O)(C)C.[CH3:46][O:47][C:48]1[CH:65]=[CH:64][C:63]2[C@@H:62]3[C@H:53]([C@H:54]4[C@@:58]([CH2:60][CH2:61]3)([CH3:59])[C@@H:57](O)[CH:56]=[CH:55]4)[CH2:52][CH2:51][C:50]=2[CH:49]=1.[Cl-].[Na+]>O1CCCC1>[CH3:46][O:47][C:48]1[CH:65]=[CH:64][C:63]2[C@@H:62]3[C@H:53]([C@H:54]4[C@@:58]([CH2:60][CH2:61]3)([CH3:59])[CH:57]([O:28][C:27](=[O:29])[C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=3)[CH:56]=[CH:55]4)[CH2:52][CH2:51][C:50]=2[CH:49]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22295754HCID 22295754, compound

Product 1

HCID 66846001HCID 66846001, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

121 g triphenylphosphine, 27.1 g 4-nitrobenzoic acid, and 30.9 ml azodicarboxylic acid diisopropyl ester are added to a solution of 43.9 g of 3-methoxy-17β-hydroxyestra-1,3,5(10),15-tetraene in 1.6 l tetrahydrofuran and it is stirred for 23° C. for 2 hours. Saturated sodium chloride solution is added, it is extracted with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and evaporation of the solvent is taken up in 1.2 l acetone, 80 ml of 30% hydrogen peroxide solution is added while cooling, and after 20 minutes it is poured, while cooling, into 600 ml of semiconcentrated sodium thiosulfate solution. It is extracted with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and evaporation of the solvent is purified by recrystallization. 52.5 g of the title compound is isolated.

Workup

  1. extractionit is extracted with ethyl acetate
  2. washthe combined organic extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe residue obtained
  5. filtrationafter filtration and evaporation of the solvent
  6. addition80 ml of 30% hydrogen peroxide solution is added
  7. temperaturewhile cooling
  8. additionafter 20 minutes it is poured
  9. temperaturewhile cooling, into 600 ml of semiconcentrated sodium thiosulfate solution
  10. extractionIt is extracted with ethyl acetate
  11. washthe combined organic extracts are washed with saturated sodium chloride solution
  12. dry with materialdried over sodium sulfate
  13. customThe residue obtained
  14. filtrationafter filtration and evaporation of the solvent
  15. customis purified by recrystallization

Sources & evidence

ORD record
ord-5fd2b84263fb4745bb4e161aa45c2889
Source dataset
uspto-grants-2015_03
Patent number
US08987239B2

Reaction notes

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