Sodium Chloride → HCID 66846001, compound

HRID 467453Notes

Reaction equation

HRID 467453 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH:11]=[CH:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:41]([C:44]1[CH:52]=[CH:51][C:47]([C:48](O)=[O:49])=[CH:46][CH:45]=1)([O-:43])=[O:42].N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl-].[Na+]>O1CCCC1>[N+:41]([C:44]1[CH:45]=[CH:46][C:47]([C:48]([O:21][CH:12]2[CH:11]=[CH:10][C@H:9]3[C@H:8]4[C@H:17]([CH2:16][CH2:15][C@:13]23[CH3:14])[C:18]2[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:6][CH2:7]4)=[O:49])=[CH:51][CH:52]=1)([O-:43])=[O:42]

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

The solution of 43.9 g of 3-methoxy-17β-hydroxyestra-1,3,5(10),15-tetraene in 1.61 tetrahydrofuran is treated with 121 g of triphenylphosphine, 27.1 g of 4-nitrobenzoic acid and 30.9 ml of diisopropyl azodicarboxylate and stirred at 23° C. for 2 hours. This is treated with saturated sodium chloride solution, extracted with ethyl acetate, and the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and solvent removal is taken up 1.2 l acetone, treated with 80 ml of a 30% hydrogen peroxide solution with cooling, and after 20 minutes poured with cooling into 600 ml of a semi-concentrated sodium thiosulfate solution. This is extracted with ethyl acetate, and the combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after filtration and solvent removal is purified by recrystallisation. 52.5 g of the title compound are isolated.

Workup

  1. extractionextracted 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 solvent removal
  6. additiontreated with 80 ml of a 30% hydrogen peroxide solution
  7. temperaturewith cooling
  8. additionafter 20 minutes poured
  9. temperaturewith cooling into 600 ml of a semi-concentrated sodium thiosulfate solution
  10. extractionThis 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 solvent removal
  15. customis purified by recrystallisation

Sources & evidence

ORD record
ord-5596620960c34ab1b1f43852351e4fcd
Source dataset
uspto-grants-2014_01
Patent number
US08623850B2

Reaction notes

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