(Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide → 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxotetrahydrofuran-3-yl)methyl)phenyl)acetamide

HRID 1256162Notes

Reaction equation

HRID 1256162 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:8](/[CH:26]=[C:27]2\[C:28](=[O:32])[O:29][CH2:30][CH2:31]\2)[CH:7]=1)=[O:4]>CO.[Pd]>[F:34][C:2]([F:1])([F:33])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:8]([CH2:26][CH:27]2[CH2:31][CH2:30][O:29][C:28]2=[O:32])[CH:7]=1)=[O:4]

Participants

4

Reactant 1

HCID 86655230(Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide

Product 1

HCID 866552322,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxotetrahydrofuran-3-yl)methyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(Z)-2,2,2-Trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide (200 mg) was hydrogenated with Pd/C (10%, 50 mg) in MeOH (20 ml) at 30 psi for 2 hrs. The reaction mixture was filtered, concentrated in reduced pressure to dryness. The crude product was treated with DCM to give 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxotetrahydrofuran-3-yl)methyl)phenyl)acetamide as a solid. 1H NMR (400 MHz, CD3OD) δ (ppm): 7.92 (d, J=8.6 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.64 (dd, J=8.2, 2.4 Hz, 1H), 7.28 (s, 1H), 7.22 (d, J=8.2 Hz, 1H), 7.17 (dd, J=8.2, 2.0 Hz, 1H), 4.95 (s, 2H), 4.36 (dt, J=8.8, 2.8 Hz, 1H), 4.19 (m, 1H), 3.53 (m, 1H), 3.06 (m, 2H), 2.22 (m, 1H), 2.04 (m, 1H). MS (ESI) m/z=497 (M−1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in reduced pressure to dryness
  3. additionThe crude product was treated with DCM

Sources & evidence

ORD record
ord-b8f98b824b1e455fbc88e3700f89fba8
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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