Methanol → 2-(2-Trifluoromethyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047919ノート

反応式

HRID 1047919 の反応式
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.O>CO.C(Cl)Cl>[F:24][C:23]([F:25])([F:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:27]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 312751,4-DioxaneHCID 593143762-(2-Trifluoromethyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

生成物 1

HCID 593143322-(2-Trifluoromethyl-benzoylamino)-indan-2-carboxylic acid収率 97,336.5%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

A 100 mL flask containing 2-(2-trifluoromethyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (324, 0.57 g, 1.5 μmol) is charged with 1,4-dioxane (9 mL) and MeOH (9 mL). A stirring bar is added and stirring is initiated. After dissolution, water (4.5 mL) is added followed by the LiOH monohydrate (160 mg, 3.81 mmol). After 110 h, tlc analysis (silica, 10% MeOH/DCM) indicates that the starting material is completely consumed. The pH of the reaction mixture is carefully adjusted to pH 2 by slowly adding dilute aqueous HCl (3%, ˜9 mL). The contents of the flask are poured into a separatory funnel which contains EtOAc (40 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic phases are washed with water (20 mL) and brine (20 mL), and then dried over MgSO4, filtered and concentrated by pumping to constant weight yields off white solid (0.51 g, 97%).

後処理

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionby slowly adding dilute aqueous HCl (3%, ˜9 mL)
  5. additionThe contents of the flask are poured into a separatory funnel which
  6. customThe layers are separated
  7. extractionThe aqueous layer is extracted with EtOAc (20 mL)
  8. washThe combined organic phases are washed with water (20 mL) and brine (20 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-713c78af71074b558fb8d5a53f3bc748
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

読み込み中…