Hydrochloric Acid → HCID 53734384, compound

HRID 2256475Notes

Reaction equation

HRID 2256475 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:18])([CH2:12][O:13][C:14](=[O:17])[CH2:15][CH3:16])[CH2:10][OH:11].[CH3:19][S:20](Cl)(=[O:22])=[O:21].N1C=CC=CC=1.Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:18])([CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:12][O:13][C:14](=[O:17])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 53840423HCID 53840423, compound

Product 1

HCID 53734384HCID 53734384, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a solution wherein 0.5 g (R)-2-(2,4-difluorophenyl)-3-propionyloxy-1,2-propanediol obtained in Example 37 was dissolved in 5 ml of ethyl acetate was added dropwise 0.66 g of methanesulfonyl chloride at a temperature of 0° to 5° C., and thereto was added dropwise 0.46 g of pyridine at a temperature of 0° to 5° C. After dropping, the resulting liquid was stirred at room temperature for 16 hours. To the reaction mixture was added 20 ml of 1N hydrochloric acid and an organic layer separated. The organic layer was washed with saturated aqueous solution with sodium hydrogencarbonate and with saturated aqueous solution with sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give 0.53 g of oily (S)-2-(2,4-difluorophenyl)-1-propionyloxy-3-methanesulfonyloxy-2-propanol. An optical purity thereof was determined in the same manner as in Example 35. (Elution time: 24.3 minutes ((R)-form) and 26.9 minutes ((S)-form)).

Workup

  1. customan organic layer separated
  2. washThe organic layer was washed with saturated aqueous solution with sodium hydrogencarbonate and with saturated aqueous solution with sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3c141fb32f724befbc7cb956948b69a3
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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