Water → HCID 68525644, compound

HRID 1932539Notes

Reaction equation

HRID 1932539 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:5]([NH:7][C:8]1[CH:32]=[CH:31][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:30])[CH2:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])=[CH:15][CH:14]=2)=[C:10]([F:33])[CH:9]=1)=[O:6].[BH4-].[Na+].O.[Cl-].[NH4+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:5]([NH:7][C:8]1[CH:32]=[CH:31][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH:19]([OH:30])[CH2:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])=[CH:17][CH:18]=2)=[C:10]([F:33])[CH:9]=1)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68527038HCID 68527038, compound

Product 1

HCID 68525644HCID 68525644, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(4-{4-[4-(3,4-dichlorobenzoylamino)-2-fluorophenoxy]phenyl}-4-oxobutyryl)morpholine (1.00 g, 1.83 mmol) in THF (20 mL) and methanol (5 mL) was added sodium borohydride (0.0694 g, 1.83 mmol), and the resulting solution was stirred for 1 hour at room temperature. To this reaction solution were added water and saturated aqueous ammonium chloride, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1). The obtained solid was recrystallized from water-containing isopropanol, to thereby yield 0.850 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  6. customThe obtained solid was recrystallized from water-
  7. additioncontaining isopropanol

Sources & evidence

ORD record
ord-e0132789a6aa446d91163be9fdd8b354
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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