Hydrochloric Acid → HCID 86593274, compound

HRID 1610595Notes

Reaction equation

HRID 1610595 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=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:42]=[CH:41][CH:40]=[CH:39][N:38]=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 22261486HCID 22261486, compound

Product 1

HCID 86593274HCID 86593274, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (3.19 g, 23.4 mmol) in diethyl ether (100 ml) was added sodium borohydride (1.77 g, 67.1 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off, and to the filtrate was added a solution of benzyl 3-oxo-3-[4-(pyridin-2-yloxy)phenyl]-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (6.5 g, 11.7 mmol) in diethyl ether (50 ml) 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 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=2:1-1:1) to give the objective substance (4.78 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=2:1-1:1)
  9. customto give the objective substance (4.78 g, 73%)

Sources & evidence

ORD record
ord-a89bd88ec4e046a2aa1663a646743358
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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