Hydrochloric Acid → HCID 178440858、化合物

HRID 1057174ノート

反応式

HRID 1057174 の反応式
[Li+].[OH-].[NH:3]1[C:7]2[CH:8]=[CH:9][C:10](/[C:12](/[C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([O:32]CC)=[O:31])=[CH:24][CH:23]=3)=[C:13](/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)\[CH2:14][CH3:15])=[CH:11][C:6]=2[N:5]=[N:4]1.Cl>C1COCC1.CCO.O>[NH:3]1[C:7]2[CH:8]=[CH:9][C:10](/[C:12](/[C:22]3[CH:23]=[CH:24][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)=[C:13](/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)\[CH2:14][CH3:15])=[CH:11][C:6]=2[N:5]=[N:4]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178470902HCID 178470902、化合物

生成物 1

HCID 178440858HCID 178440858、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

An aqueous solution of LiOH (0.22 g, 9.4 mmol) was added to a solution of (E)-ethyl 3-(4-((E)-1-(1H-benzo[d][1,2,3]triazol-5-yl)-2-phenylbut-1-en-1-yl)phenyl)acrylate (0.2 g, 0.47 mmol) in THF-EtOH (1:1, 24 mL) at room temperature, and the resulting mixture was stirred overnight. The reaction was monitored by LCMS. Upon completion, 1N aqueous HCl was added until the pH was 3. Then, the mixture was diluted with water and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (100 mL), washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give the crude product. This crude material was purified on a silica gel column eluted with 0-20% methanol in dichloromethane affording the title compound as an off-white solid (0.12 g). 1H NMR (300 MHz, DMSO-d6): δ 15.65 (br, 1H), 12.29 (br, 1H), 7.92 (d, 1H), 7.78 (s, 1H), 7.48-7.35 (m, 3H), 7.24-7.13 (m, 7H), 6.91 (d, 2H), 6.37 (d, 1H), 2.39 (q, 2H), 0.89 (t, 3H); LCMS: 396 (M+H)+.

後処理

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with water (100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c22857e210204446b344bac729af8c01
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

反応ノート

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