Hydrochloric Acid → HCID 86593277, compound

HRID 1610603Notes

Reaction equation

HRID 1610603 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:32][CH:31]=1)[CH:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])[CH:18]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].Cl.C(=O)([O-])O.[Na+]>C(OCC)C.[Cl-].[Zn+2].[Cl-].O>[OH:3][CH:4]([C:30]1[CH:31]=[CH:32][C:33]([O:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:34][CH:35]=1)[CH:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])[CH:18]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22262248HCID 22262248, compound

Product 1

HCID 86593277HCID 86593277, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (2.95 g, 21.6 mmol) in diethyl ether (100 ml) was added sodium borohydride (1.64 g, 43.3 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off, and a solution of benzyl 3-oxo-3-[4-(pyridin-3-yloxy)phenyl]-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (6.0 g, 10.8 mmol, crude) in diethyl ether (50 ml) was added to the filtrate at 0° C. The mixture was stirred for 30 min. and 1N hydrochloric acid was added to stop the reaction. After neutralization with saturated aqueous sodium hydrogen carbonate, water (200 ml) was further added and the mixture was extracted with ethyl acetate (200 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=2:1) and recrystallized from ethyl acetate-hexane to give the objective substance (3.13 g, 73%).

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 (200 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=2:1)
  9. customrecrystallized from ethyl acetate-hexane
  10. customto give the objective substance (3.13 g, 73%)

Sources & evidence

ORD record
ord-ee33d1d5f5714751809162ba1a194db0
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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