Hydrochloric Acid → HCID 86593262, compound

HRID 1610559Notes

Reaction equation

HRID 1610559 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:31])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[N:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:31])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:29])([F:30])[CH:26]([F:27])[F:28])[N:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22262308HCID 22262308, compound

Product 1

HCID 86593262HCID 86593262, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (915 mg, 6.71 mmol) in diethyl ether (20 ml) was added sodium borohydride (508 mg, 13.4 mmol), and the mixture was-stirred at room temperature for 30 min. Insoluble material was filtered off, and a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-{[6-(1,1,2,2-tetrafluoroethoxy)pyridin-2-yl]methyl}propanoate (1.40 g, 3.35 mmol) in diethyl ether (10 ml) was added to the filtrate at 0° C. The mixture was stirred for 30 min. and 1N hydrochloric acid was added to the reaction solution to stop the reaction. Then, water (50 ml) was added and the mixture was extracted with ethyl-acetate (50 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1) to give the objective substance (1.28 g, 91%).

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringThe mixture was stirred for 30 min.
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl-acetate (50 ml×2)
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1)
  9. customto give the objective substance (1.28 g, 91%)

Sources & evidence

ORD record
ord-99a44d161218420d952761922c67b921
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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