Methanol → HCID 66925170, compound

HRID 554449Notes

Reaction equation

HRID 554449 reaction equation
C(O[C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]([S:16]([C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])(=[O:18])=[O:17])[CH:15]=1)C)=O)(C)(C)C.C(OCC)(=O)C.[ClH:40].CO>C(OCC)(=O)C>[ClH:40].[CH3:6][NH:8][CH2:10][C:11]1[CH:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]([S:16]([C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])(=[O:18])=[O:17])[CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 66924919HCID 66924919, compound

Product 1

HCID 66925170HCID 66925170, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[(4-{[(tert-Butoxycarbonyl)(methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoic acid (256 mg) was dissolved in ethyl acetate (1 mL), and 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added at room temperature. After stirring at the same temperature for 3 hr, the reaction mixture was homogenized with methanol, activated carbon was added and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate. The obtained crystal was recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as colorless crystals (yield 110 mg, 50%).

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was crystallized from ethyl acetate
  5. customThe obtained crystal was recrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-31b56f10883a48cfb3c9d725233d7a95
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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