Hydrogen chloride-ethyl acetate → HCID 67396633, compound

HRID 1426833Notes

Reaction equation

HRID 1426833 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[S:17][C:18]([C:21]4[O:25][N:24]=[CH:23][CH:22]=4)=[CH:19][CH:20]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:26][N:27](C)[C:28](=O)OC(C)(C)C)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(OCC)(=O)C.[ClH:42]>C(O)C>[ClH:42].[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[S:17][C:18]([C:21]4[O:25][N:24]=[CH:23][CH:22]=4)=[CH:19][CH:20]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:26][NH:27][CH3:28])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67398445HCID 67398445, compound

Product 1

HCID 67396633HCID 67396633, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl ({5-(2-fluoropyridin-3-yl)-1-[(5-isoxazol-5-yl-2-thienyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (80 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 50° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from a mixed solvent of ethyl acetate-diethyl ether (1:1) to give the title compound as colorless crystals (yield 23 mg, 33%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from a mixed solvent of ethyl acetate-diethyl ether (1:1)

Sources & evidence

ORD record
ord-57b3844ebf564c80993aeed3e70e1c61
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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