Water → HCID 86718262, compound

HRID 922741Notes

Reaction equation

HRID 922741 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[C:13]3([CH2:14][OH:15])[C:10]([CH3:16])([CH2:11][O:12]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:13]3([CH2:14][O:15][S:27]([CH3:26])(=[O:29])=[O:28])[C:10]([CH3:16])([CH2:11][O:12]3)[CH2:9][CH2:8]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86718260HCID 86718260, compound

Product 1

HCID 86718262HCID 86718262, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 6 ml of toluene, 300 mg of Compound 8a-1 synthesized in Production Example 19 was dissolved. To the solution thus obtained, 235 μl of triethylamine and 122 μl of methanesulfonyl chloride were added, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was carried out. The organic layer thus extracted was washed with an aqueous solution of hydrochloric acid, an aqueous solution of sodium hydrogen carbonate, and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 378.3 mg of Compound 9a-1-1.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. extractionextraction with ethyl acetate
  6. extractionThe organic layer thus extracted
  7. washwas washed with an aqueous solution of hydrochloric acid
  8. dry with materialan aqueous solution of sodium hydrogen carbonate, and saturated brine, and then dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled away
  10. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b21adf375e9400a914ed8f8f323d9bd
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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