Water → tert-butyl{[5-(3-cyano-2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 1782355Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution (5 mL) of tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (150 mg) in tetrahydrofuran were added triethylamine (93 mg) and methanesulfonyl chloride (84 mg) at room temperature. The reaction mixture was stirred at 70° C. for 8 hr, and cooled to room temperature. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1) to give the title compound as a pale-yellow oil (yield 106 mg, 73%).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1)

Sources & evidence

ORD record: ord-26031506c17e4b9db5e5157307bed460
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498337B2

Reaction notes

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