Hydrochloric Acid → tert-butyl [(4-fluoro-5-(2-fluoropyridin-3-yl)-1-{[5-(1-hydroxyethyl)-2-furyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamate

HRID 1426742Notes

Reaction equation

HRID 1426742 reaction equation
[F:1][C:2]1[C:3]([CH2:24][N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:4][N:5]([S:14]([C:17]2[O:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:34][Mg]Br.Cl>O1CCCC1>[F:1][C:2]1[C:3]([CH2:24][N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[CH:4][N:5]([S:14]([C:17]2[O:18][C:19]([CH:22]([OH:23])[CH3:34])=[CH:20][CH:21]=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 3

HCID 313Hydrochloric AcidHCID 86624000tert-butyl ({4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-formyl-2-furyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 67397408tert-butyl [(4-fluoro-5-(2-fluoropyridin-3-yl)-1-{[5-(1-hydroxyethyl)-2-furyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl ({4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-formyl-2-furyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (464 mg) in tetrahydrofuran (5 mL) was added a 1.0 mol/L solution (1.3 mL) of methylmagnesium bromide in tetrahydrofuran under ice-cooling and the mixture was stirred for 2 hr. 1 mol/L Hydrochloric acid was added to the reaction mixture and the mixture was further stirred for 1 hr and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→3:2) to give the title compound as a pale-yellow oil (yield 410 mg, 86%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionextracted with ethyl acetate
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→3:2)

Sources & evidence

ORD record
ord-5be6c0faa5ce4cfeae384ef6adb90a3f
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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