Hydrochloric Acid → HCID 22261558, compound

HRID 1610587Notes

Reaction equation

HRID 1610587 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][CH:38]=2)=[CH:32][N: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:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][N: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]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22261706HCID 22261706, compound

Product 1

HCID 22261558HCID 22261558, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (4.57 g, 33.6 mmol) in diethyl ether (100 ml) was added sodium borohydride (2.54 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-(5-phenoxypyridin-2-yl)-2-[3-(1,1,2,2-tetrafluoroethoxy)-benzyl]propanoate (9.32 g, 16.8 mmol, crude) in diethyl ether (100 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 further added and the mixture was extracted with ethyl acetate (500 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 (5.07 g, 54%, crude). The present compound was used for the next reaction as a crude compound.

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 (500 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 (5.07 g, 54%, crude)

Sources & evidence

ORD record
ord-23e1f7b5f2e348dd909e6c90849e016d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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