Hydrochloric Acid → HCID 68712747, compound

HRID 1696710Notes

Reaction equation

HRID 1696710 reaction equation
[F-].[Cs+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:8]([SH:13])=[N:9][CH:10]=[CH:11][CH:12]=1.CS(O[C@H:19]([CH3:38])[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=[O:21])(=O)=O.Cl>CN(C=O)C.O>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([C:20](=[O:21])[C@@H:19]([S:13][C:8]3[C:7]([O:6][CH2:5][O:4][CH3:3])=[CH:12][CH:11]=[CH:10][N:9]=3)[CH3:38])=[CH:23][CH:24]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 86643131HCID 86643131, compound2×HCID 178498117HCID 178498117, compound

Product 1

HCID 68712747HCID 68712747, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dried cesium fluoride (5.31 g, 35.0 mmol) and 3-(methoxymethoxy)pyridine-2-thiol (6.0 g, 35.0 mmol) synthesized in Reference Example 15 were dissolved in DMF (120 mL), and under stirring with cooling with ice, (1R*)-2-{4-[(4-methoxybenzyl)oxy]phenyl}-1-methyl-2-oxoethyl methanesulfonate (11.58 g, 31.8 mmol) synthesized in the above (4) was added. The reaction solution was stirred for 20 hours with cooling with ice, then 2 N HCl (20 mL) and water (180 mL) were added, and further stirred for 20 minutes with cooling with ice. The formed solid was collected by filtration, washed with water, and dried under reduced pressure to obtain the entitled compound (13.3 g, containing 20% side product) as a milky white solid.

Workup

  1. additionwas added
  2. stirringThe reaction solution was stirred for 20 hours
  3. temperaturewith cooling with ice
  4. stirringfurther stirred for 20 minutes
  5. temperaturewith cooling with ice
  6. filtrationThe formed solid was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure
  9. customto obtain

Sources & evidence

ORD record
ord-a9d84015c873485f9c58846cf85f7c11
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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