Sodium Hydroxide → 4-amino-2-fluoro-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

HRID 1256064ノート

反応式

HRID 1256064 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:22]C(=O)C)[CH:5]=[CH:6][C:7]=1[S:8](=[O:21])(=[O:20])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1.[OH-].[Na+]>O1CCOCC1.Cl>[NH2:22][C:4]1[CH:5]=[CH:6][C:7]([S:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:17][O:16][B:15]([OH:18])[C:14]=3[CH:19]=2)(=[O:20])=[O:21])=[C:2]([F:1])[CH:3]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67174565N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide

生成物 1

HCID 671745464-amino-2-fluoro-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide収率 14%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide (1.45 g, 3.98 mmol) in 1,4-dioxane (8 mL) and concentrated hydrochloric acid (2 mL) was refluxed at 100° C. for three hours. The solution was cooled to room temperature and neutralized to pH 5 using 3 N sodium hydroxide. The solution was extracted using ethyl acetate and water. The organic layer was washed three times with water, than washed with brine, dried over sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by silica column via CombiFlash using dichloromethane and methanol. The desired fractions were collected and the solvent was removed under reduced pressure. Water and toluene were added and removed under reduced pressure. Diisopropyl ether was used to transfer powder from round bottom flask to Buckner funnel to give 4-amino-2-fluoro-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (0.176 g, 14% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 4.85 (s, 2H), 6.23-6.31 (m, 4H), 7.16 (dd, J=2.1 Hz, J=8.1 Hz, 1H), 7.22 (d, J=8.3 Hz, 1H), 7.36 (t, J=8.6 Hz, 1H), 7.43 (d, J=1.8 Hz, 1H), 9.17 (s, 1H), 10.06 (s, 1H).

後処理

  1. extractionThe solution was extracted
  2. washThe organic layer was washed three times with water
  3. washthan washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica column via CombiFlash
  8. customThe desired fractions were collected
  9. customthe solvent was removed under reduced pressure
  10. additionWater and toluene were added
  11. customremoved under reduced pressure

出典と根拠

ORDレコード
ord-6cf5e35c528d416784367eadfe8718d8
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

反応ノート

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