Hydrochloric Acid → HCID 86657926, compound

HRID 1186306Notes

Reaction equation

HRID 1186306 reaction equation
[F:1][C:2]([F:36])([F:35])[CH:3]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[O:4][C:5]1[C:6]([NH:15][S:16](=[O:28])(=[O:27])[NH:17][CH2:18][CH2:19][CH:20](OCC)[O:21]CC)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1>[F:36][C:2]([F:1])([F:35])[CH:3]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[O:4][C:5]1[C:6]([NH:15][S:16](=[O:27])(=[O:28])[NH:17][CH2:18][CH2:19][CH:20]=[O:21])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67403140HCID 67403140, compound

Product 1

HCID 86657926HCID 86657926, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 272 (72.0 mg, 0.136 mmol) obtained in Example 266 was dissolved in THF (1.50 mL). To this, a 1.00 mol/L aqueous hydrochloric acid solution (1.50 mL) was added and the mixture was stirred at room temperature for 1.5 hours. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 1/1) to give Compound 273 (41.6 mg, yield: 67%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 1/1)

Sources & evidence

ORD record
ord-7aa9610c5bf04fa48527d9753ebaedf1
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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