Hydrochloric Acid → HCID 66939684, compound

HRID 1257377Notes

Reaction equation

HRID 1257377 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)=[N:4][C:3]=1[C:17](O)=[O:18].B.O1CCCC1.Cl>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)=[N:4][C:3]=1[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 23563101HCID 23563101, compound

Product 1

HCID 66939684HCID 66939684, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (5 mL) of the compound (310 mg, 1.1 mmol) obtained in Example 71a in tetrahydrofuran was added borane-tetrahydrofuran complex (1.1 M tetrahydrofuran solution, 3.0 mL, 3.3 mmol), and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=65/35) to give the title compound (82 mg, 27%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=65/35)

Sources & evidence

ORD record
ord-e3d68e50df2a44f9a7a85f79ba738dbe
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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