Hydrochloric Acid → HCID 68525810, compound

HRID 884143Notes

Reaction equation

HRID 884143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])=[CH:17][CH:16]=2)=[N:12][CH:13]=1)=[O:6].[BH4-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][C:8]1[CH:13]=[N:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68525138HCID 68525138, compound

Product 1

HCID 68525810HCID 68525810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-{4-[5-(3,4-dichloro-benzoylamino)pyridin-2-yloxy]phenyl}pentanoate (8.79 g, 18.0 mmol) in THF (140 mL) was added sodium borohydride (3.14 g, 144 mmol), and the resulting solution was refluxed for 3 hours under a nitrogen atmosphere. The resulting reaction solution was cooled with ice, and treated with 1 N hydrochloric acid. The resulting solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2), to thereby yield 7.07 g of the title compound.

Workup

  1. temperaturethe resulting solution was refluxed for 3 hours under a nitrogen atmosphere
  2. customThe resulting reaction solution
  3. temperaturewas cooled with ice
  4. extractionThe resulting solution was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d74456e428d740fc90fa39ab4ea4959e
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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