Sulfuric Acid → HCID 86718261, compound

HRID 922744Notes

Reaction equation

HRID 922744 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]2[C:13]3([C:14]([OH:16])=[O:15])[C:10]([CH3:17])([CH2:11][O:12]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.Cl.[CH2:25](N(CC)CC)C.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.CO.C(N(CC)CC)C.O1CCCC1>[CH3:25][O:15][C:14]([C:13]12[O:12][CH2:11][C:10]1([CH3:17])[CH2:9][CH2:8][CH:7]2[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=1)=[O:16]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 11130Triethylamine hydrochlorideHCID 24386Thionyl ChlorideHCID 86718263HCID 86718263, compound

Product 1

HCID 86718261HCID 86718261, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

In 2 ml of toluene, 50 mg of Compound 13-1 synthesized in Production Example 26 was dissolved. To the solution thus obtained, 0.06 ml of triethylamine was added, and the resulting mixture solution was then cooled. To the solution thus cooled, 0.02 ml of thionyl chloride was added, and the resulting mixture solution was stirred for 1 hour while being allowed to reach room temperature. After the reaction, triethylamine hydrochloride generated was removed by filtration from the reaction solution, and the solvent was then distilled away under a reduced pressure to obtain 73 mg of crude product. To the crude product, 2 ml of tetrahydrofuran, 0.05 ml of triethylamine, and 0.05 ml of methanol were added, and the resulting mixture was stirred at room temperature for 0.5 hour. After the reaction, an aqueous solution of diluted sulphuric acid was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away under a reduced pressure to obtain 58 mg of Compound 7-1.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. temperaturethe resulting mixture solution was then cooled
  4. temperatureTo the solution thus cooled
  5. customto reach room temperature
  6. customgenerated was removed by filtration from the reaction solution
  7. distillationthe solvent was then distilled away under a reduced pressure
  8. customto obtain 73 mg of crude product
  9. stirringthe resulting mixture was stirred at room temperature for 0.5 hour
  10. customAfter the reaction
  11. customthus obtained
  12. extractionextraction with ethyl acetate
  13. washThe organic layer was washed with saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. distillationThe solvent was distilled away under a reduced pressure

Sources & evidence

ORD record
ord-e24133c894a44eee940451681660c278
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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