Boron trifluoride etherate → HCID 44404785, 화합물

HRID 2084933노트

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HRID 2084933 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:17][CH:16]2[C:18]([O:20][CH3:21])=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Br:22][CH2:23][CH2:24][OH:25].B(F)(F)F.CCOCC>C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[CH:16]([NH:15][S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[CH2:17][O:25][CH2:24][CH2:23][Br:22]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 108982-BromoethanolHCID 86587129HCID 86587129, 화합물

생성물 1

HCID 44404785HCID 44404785, 화합물수율 26%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a 0° solution of 1-({[4-(2-butynyloxy)phenyl]sulfonyl}-2-aziridinecarboxylic acid, methyl ester (0.55 g, 1.78 mmol) in 2-bromoethanol (1.26 mL, 17.8 mmol) was dropwise added boron trifluoride etherate (0.18 mL). The mixture was stirred at 0° C. for 30 minutes and stirred at room temperature for 6 hours. The reaction was diluted with ethyl acetate. The organic layer was washed with 1N NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (7:3) to obtain 0.2 g of 3-(2-bromo-ethoxy)-2-(4-[2-butynyloxy]-benzenesulfonylamino)-propionic acid methyl ester. Yield: 26%. mp 45-46° C. Electrospray Mass Spec 434.1.436.1 (M+H)+.

후처리

  1. customTo a 0°
  2. stirringstirred at room temperature for 6 hours
  3. washThe organic layer was washed with 1N NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (7:3)

출처 및 근거

ORD 기록
ord-7b8d55859b0b477fbe5574d3815e5392
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716833B2

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