Hydroxylamine → Cimlanod

HRID 1749190ノート

反応式

HRID 1749190 の反応式
[NH2:1][OH:2].O.[CH3:4][C:5]1[O:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][CH:6]=1.CCCCCC>C1COCC1.C(OCC)(=O)C>[OH:2][NH:1][S:10]([C:8]1[O:9][C:5]([CH3:4])=[CH:6][CH:7]=1)(=[O:12])=[O:11]

参加物

7

反応物 4

HCID 787HydroxylamineHCID 962WaterHCID 8058HexaneHCID 178643615-Methylfuran-2-sulfonyl chloride

生成物 1

HCID 76685198Cimlanod収率 61%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of hydroxylamine (0.92 mL of a 50% aqueous solution; 13.8 mmol) in THF (6 mL) and water (2 mL) cooled to 0° C. was added 5-methylfuran-2-sulfonyl chloride (1 g, 5.5 mmol) as a solution in THF (6 mL) dropwise so as to maintain the temperature below 10° C. The reaction was stirred for 5 minutes, after which time TLC (1:1 hexane:ethyl acetate (H:EA)) showed substantially complete consumption of the sulfonyl chloride. The reaction was diluted twice with 50 mL dichloromethane (DCM) and the organic portion was separated and washed with water (10 mL). The organic portion was dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was chromatographed by silica gel chromatography eluting with heptanes:EtOAc followed by trituration with heptane to provide the title compound as a yellow solid (0.59 g, yield 61%). LC-MS tR=0.91 min; 1H NMR (DMSO, 500 MHz) δ ppm 9.82 (1H, d, J=3.1 Hz), 9.64 (1H, d, J=3.2 Hz), 7.10 (1H, d, J=3.4 Hz), 6.36 (1H, d, J=3.4 Hz), 2.36 (3H, s).

後処理

  1. temperatureto maintain the temperature below 10° C
  2. customconsumption of the sulfonyl chloride
  3. additionThe reaction was diluted twice with 50 mL dichloromethane (DCM)
  4. customthe organic portion was separated
  5. washwashed with water (10 mL)
  6. dry with materialThe organic portion was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was chromatographed by silica gel chromatography
  10. washeluting with heptanes

出典と根拠

ORDレコード
ord-b184672adac24602a6330ec3ad8df96d
出典データセット
uspto-grants-2015_10
特許番号
US09156804B2

反応ノート

読み込み中…