Hydrochloric Acid → HCID 68283667, compound

HRID 541490Notes

Reaction equation

HRID 541490 reaction equation
C(O[CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH2:7][CH2:6]1)(=O)C.[OH-].[Na+].Cl>CO.O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14]([CH:5]=[CH:6][CH2:7][CH:8]2[CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71534205HCID 71534205, compound

Product 1

HCID 68283667HCID 68283667, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of the compound obtained in Step D (261 mg, 0.86 mmol) in a mixture of methanol/water (2/0.2 mL) at ambient temperature there is added sodium hydroxide (86 mg, 2.14 mmol). The mixture is stirred for 1 hour under reflux, and the solution is then cooled. Hydrochloric acid (2.6 mL, 2.6 mmol, 1N) is added and the mixture is stirred overnight. The aqueous phase is extracted with dichloromethane, and the organic phases are washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated. The title compound is obtained after purification by flash column chromatography (ethyl acetate-petroleum ether: 90-10, then ethyl acetate-methanol: 90-10) in the form of an oil in a yield of 61%.

Workup

  1. temperatureunder reflux
  2. temperaturethe solution is then cooled
  3. stirringthe mixture is stirred overnight
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. washthe organic phases are washed with saturated NaCl solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f5ac5f1e37a04c4eae34493c9fbbb71d
Source dataset
uspto-grants-2014_10
Patent number
US08871975B2

Reaction notes

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