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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 1627316
ノート
印刷プレビュー

反応式

HRID 1627316 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
65 °C

実験手順

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) m/z 553.5 [M+H]+.

後処理

  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%)

出典と根拠

ORDレコード
ord-cddc9f84836f4ad09edc4baa9f0e9730
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785488B2

反応ノート

読み込み中…

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