Hydrochloric Acid → HCID 178440858, 화합물

HRID 1057174노트

반응식

HRID 1057174 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178470902HCID 178470902, 화합물

생성물 1

HCID 178440858HCID 178440858, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c22857e210204446b344bac729af8c01
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

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