Hydroxylamine → Cimlanod

HRID 1749190노트

반응식

HRID 1749190 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 76685198Cimlanod수율 61%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b184672adac24602a6330ec3ad8df96d
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156804B2

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