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

HRID 1047919노트

반응식

HRID 1047919 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-713c78af71074b558fb8d5a53f3bc748
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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