Hydrochloric Acid → 5-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid

HRID 1039201ノート

反応式

HRID 1039201 の反応式
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])=[CH:11][N:12]=1.[Li+].[OH-].Cl>O1CCOCC1.O>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([OH:20])=[C:13]([C:10]2[O:9][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[N:12][CH:11]=2)[CH:18]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 684878995-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

生成物 1

HCID 684943605-[5-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid収率 60.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Dissolve 5-[5-(5-chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.26 g, 10.52 mmol) in 50 mL of dioxane and add a solution of LiOH (1.2671 g, 50.91 mmol) in 25 mL of water to it. Allow the reaction to stir at ambient temperature for 18 hours. Acidify the reaction with 5N HCl and concentrate the reaction mixture in vacuo to remove the dioxane. Extract the aqueous residue with EtOAc (3×). Dry the combined organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford a crude residue. Triturate the residue in cold EtOAc. Collect the product via filtration to afford 1.8837 g of the titled product (60%): mass spectrum: m/z=296.1 (M+H).

後処理

  1. customthe reaction
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto remove the dioxane
  4. extractionExtract the aqueous residue with EtOAc (3×)
  5. dry with materialDry the combined organic layers with MgSO4
  6. filtrationFilter off the drying agent
  7. concentrationconcentrate in vacuo
  8. customto afford a crude residue
  9. customTriturate the residue in cold EtOAc
  10. customCollect the product
  11. filtrationvia filtration

出典と根拠

ORDレコード
ord-cd112616fc6349659a26fe140b2bacce
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

読み込み中…