Hydrochloric Acid → Diisopropylether ethyl acetate

HRID 2194299Notes

Reaction equation

HRID 2194299 reaction equation
[OH-].[Na+].O1CCC[CH2:4]1.COC1C=C(C=CC=1OC[C:39]1N=[C:41]([C:45]2C=CC=CC=2)[O:42][C:43]=1[CH3:44])CN1C2C=CC=C(O[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])C=2C2C1=CC=CC=2.Cl>O.CO>[C:29]([O:31][CH2:32][CH3:33])(=[O:30])[CH3:28].[CH:41]([O:42][CH:43]([CH3:39])[CH3:44])([CH3:45])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59571731ethyl 2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}acetate

Product 1

HCID 22281796Diisopropylether ethyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1 mL of 5 N sodium hydroxide solution was added to tetrahydrofuran:methanol=1:1 (10 mL) solution of 107 mg of ethyl 2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}acetate, and stirred at room temperature for 1 hour. The reaction mixture was diluted with water, adjusted to pH3 by 1 N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The crystals of residue were isolated by filtration with ethyl acetate-diisopropylether, dried under reduced pressure, and 74 mg of the subject compound was prepared as pale yellow crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-310f2b5a410a4c1d922cf331353a241e
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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