Hydrochloric Acid → KR-33494

HRID 547513Notes

Reaction equation

HRID 547513 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[CH:8][N:7]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH2:12][C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][N:7]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:8]=2)=[O:21])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59234712HCID 59234712, compound

Product 1

HCID 25009726KR-33494Yield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.2 mM) of the compound obtained in Example 1 was dissolved in 1 ml of methanol to which 0.3 ml (0.3 mM, 1.5 eq) of 1N sodium hydroxide was added dropwise, and the resulting mixture was heated with stirring under a nitrogen atmosphere for 1 hour. The resultant was acidified with 1N hydrochloric acid solution, and extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure, to obtain 90 mg (91.5%) of the title compound.

Workup

  1. additionwas added dropwise
  2. temperaturethe resulting mixture was heated
  3. extractionextracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-66f88ff83c7d4c028f7916c615ca13e0
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

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