Boron trifluoride etherate → HCID 44404785、化合物

HRID 2084933ノート

反応式

HRID 2084933 の反応式
[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]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 108982-BromoethanolHCID 86587129HCID 86587129、化合物

生成物 1

HCID 44404785HCID 44404785、化合物収率 26%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-7b8d55859b0b477fbe5574d3815e5392
出典データセット
uspto-grants-2004_04
特許番号
US06716833B2

反応ノート

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