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Hydrochloric Acid → 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoic acid

HRID 83923
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인쇄 미리보기

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HRID 83923 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:37])[C:11]=1[O:12][CH2:13][C:14]1[N:15]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:16]([C:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)([CH3:21])[CH3:20])=[CH:17][N:18]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:37])[C:11]=1[O:12][CH2:13][C:14]1[N:15]([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[C:16]([C:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)([CH3:21])[CH3:20])=[CH:17][N:18]=1)[C:5]([OH:7])=[O:6]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66740309methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate

생성물 1

HCID 667402383-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoic acid수율 39%

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
65 °C

실험 절차

A mixture of methyl 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)-5-fluorobenzoate (120 mg, 0.21 mmol) and 2N NaOH (0.31 mL, 0.63 mmol) in MeOH (3 mL) was heated 3 h at 65° C. After cooling, the reaction was neutralized to pH 3 with 3N HCl, concentrated under reduced pressure, diluted with water, and then extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude material was purified by HPLC (MeCN/H2O, 10-99%) to give the title compound as an off-white solid (45 mg, 39%). MS (EI): 553.5 [M+H]+.

후처리

  1. temperatureAfter cooling
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by HPLC (MeCN/H2O, 10-99%)

출처 및 근거

ORD 기록
ord-c989eabff709493cb71096a75442fa26
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846739B2

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