Methanol → 2-(3-Methyl-2-prop-2-ynyloxy-benzoylamino)-indan-2-carboxylic acid

HRID 1047830노트

반응식

HRID 1047830 반응식
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH2:25][C:26]#[CH:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.[Li+].[OH-]>CO.C(Cl)Cl.O>[CH3:23][C:19]1[C:18]([O:24][CH2:25][C:26]#[CH:27])=[C:17]([CH:22]=[CH:21][CH:20]=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:28]

참가 물질

7

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 593141112-(3-Methyl-2-prop-2-ynyloxy-benzoylamino)-indan-2-carboxylic acid ethyl ester

생성물 1

HCID 593143512-(3-Methyl-2-prop-2-ynyloxy-benzoylamino)-indan-2-carboxylic acid수율 108%

시약·촉매·용매 2

HCID 962Water용매HCID 21226129Dichloromethane methanol용매

실험 절차

A 50 mL flask containing the 2-(3-methyl-2-prop-2-ynyloxy-benzoylamino)-indan-2-carboxylic acid ethyl ester (0.20 g, 0.53 mmol) is charged with 1,4-dioxane (3 mL) and MeOH (3 mL). A stirring bar is added and stirring is initiated. After dissolution, water (1.5 mL) is added followed by the LiOH (56 mg, 1.35 mmol). After 108 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%, ˜10 mL). The contents of the flask are poured into a separatory funnel containing EtOAc (30 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated to constant weight to give 0.2 g of off-white solid.

후처리

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionby slowly adding dilute aqueous HCl (3%, ˜10 mL)
  5. additionThe contents of the flask are poured into a separatory funnel
  6. additioncontaining EtOAc (30 mL)
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (20 mL)
  9. washThe combined organic extracts are washed with water (20 mL) and brine (20 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated to constant weight

출처 및 근거

ORD 기록
ord-7000122e95c446a9ae9682768d8e532e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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