Hydrogen chloride-ethyl acetate → HCID 67395927, compound

HRID 1426843Notes

Reaction equation

HRID 1426843 reaction equation
[F:1][C:2]1[C:3]([CH2:24][N:25](C)[C:26](=O)OC(C)(C)C)=[CH:4][N:5]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][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:40]>C(O)C>[ClH:40].[F:1][C:2]1[C:3]([CH2:24][NH:25][CH3:26])=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67396369HCID 67396369, compound

Product 1

HCID 67395927HCID 67395927, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl ({4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-hydroxyphenyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (300 mg) was dissolved in ethanol (5 mL), 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added, and the mixture was stirred at 40° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate, and further recrystallized from a mixed solvent of ethyl acetate-methanol (4:1) to give the title compound as colorless crystals (yield 208 mg, 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from ethyl acetate
  3. customfurther recrystallized from a mixed solvent of ethyl acetate-methanol (4:1)

Sources & evidence

ORD record
ord-5f1880c9821c4e728e7f16614c31067b
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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