Hydrochloric Acid → HCID 21251044, compound

HRID 1532508Notes

Reaction equation

HRID 1532508 reaction equation
C([CH:6]([C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)[CH:7]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH:35]([F:37])[F:36])[CH:25]=1)[C:8]1[CH:9]=[N:10][C:11]([N:14]([CH3:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)(OCC)=O.[Li+].[OH-].Cl>C1COCC1.CO.O>[F:37][CH:35]([F:36])[O:34][C:26]1[CH:25]=[C:24]([CH:7]([C:8]2[CH:9]=[N:10][C:11]([N:14]([CH3:23])[C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)=[CH:12][CH:13]=2)[CH2:6][C:38]2[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH:31]([F:33])[F:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21251054HCID 21251054, compound

Product 1

HCID 21251044HCID 21251044, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of the crude ester from Step 3 above in a mixture of THF/MeOH/water (4.5 mL/1.5 mL/1.5 mL), was added 1.6 mL (3.24 mmol) of a 2 N solution of LiOH. The resulting solution was stirred at 65 ° C. for 3 h, cooled down to room temperature followed by the addition of 3.4 mL of a 1.0 N HCl solution. The resulting mixture was rotovaped down to evaporate MeOH and the aqueous residue was diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layer were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Gradient 70% Ethyl acetate/hexane to 100% ethyl acetate) to afford 67 mg (47%, 2 steps) of the title compound.

Workup

  1. temperaturecooled down to room temperature
  2. customto evaporate MeOH
  3. additionthe aqueous residue was diluted with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (Gradient 70% Ethyl acetate/hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-d8fe769c19ba4d6887d3e5f63c599c30
Source dataset
uspto-grants-2001_03
Patent number
US06200993B1

Reaction notes

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