Water → Benzenesulfonamide

HRID 1063953ノート

反応式

HRID 1063953 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11]C2C=C(F)C=CC=2F)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O>C1COCC1>[C:5]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 47884524-chloro-N-(2,5-difluorophenyl)benzenesulfonamideHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 7370Benzenesulfonamide収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

To a solution of 4-chloro-N-[5-fluoro-2-fluorophenyl]benzenesulfonamide (500 mg, 1.65 mmol), triphenylphosphine (909 mg, 3.47 mmol) and 5S-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pentanol (719 mg, 3.30 mmol) in THF (7 mL) was added diisopropylazodicarboxylate (0.682 mL, 3.47 mol) dropwise at 0° C. under nitrogen. The resulting mixture was allowed to warm to 22° C. with stirring. Stirring was continued for a period of 12 h followed by the addition of 15 mL of H2O. The mixture was extracted with ether (3×15 mL). The combined organic extracts were washed with NaHCO3 and sat. brine. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (1:5 ethyl acetate:hexanes) of the concentrate afforded 466 mg of 4-chloro-N-[5-fluoro-2-flurophenyl]-N-[(R)-1-methyl-4-[(1,1-dimethylethyl)-dimethylsilyl]oxy)butyl]benzene-sulfonamide as a yellow oil in 56% yield.

後処理

  1. stirringStirring
  2. extractionThe mixture was extracted with ether (3×15 mL)
  3. washThe combined organic extracts were washed with NaHCO3 and sat. brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-da74b361c71d40b2bb9b35811ff8a13b
出典データセット
uspto-grants-2005_11
特許番号
US06967196B1

反応ノート

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