Hydrogen chloride-ethyl acetate → HCID 67398601, compound

HRID 1426811Notes

Reaction equation

HRID 1426811 reaction equation
[F:1][C:2]1[C:3]([CH2:28][N:29](C)[C:30](=O)OC(C)(C)C)=[CH:4][N:5]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:18]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.C(OCC)(=O)C.[ClH:44]>C(OCC)(=O)C.CC(O)C>[ClH:44].[F:1][C:2]1[C:3]([CH2:28][NH:29][CH3:30])=[CH:4][N:5]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:18]=2)(=[O:15])=[O:16])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67397600HCID 67397600, compound

Product 1

HCID 67398601HCID 67398601, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1-({3-[(methylsulfonyl)methyl]phenyl}sulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (266 mg) in ethyl acetate (3 mL) and 2-propanol (2 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (6 mL), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from a mixed solvent of ethanol and water to give the title compound as a white solid (yield 187 mg, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-212b949e8c30473ab8d4d914d55543c2
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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