Water → HCID 59314339, compound

HRID 1047808Notes

Reaction equation

HRID 1047808 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=2[CH3:25])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.C1COCC1.O.[Li+].[OH-]>CC(O)C.C(Cl)Cl>[CH3:24][O:23][C:19]1[C:18]([CH3:25])=[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:26]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59314241HCID 59314241, compound

Product 1

HCID 59314339HCID 59314339, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 21966342Isopropanol methylene chlorideSolvent

Procedure

A 40 mL vial containing the 2-(3-methoxy-2-methyl-benzoylamino)-indane-2-carboxylic acid ethyl ester (0.65 g, 1.84 mmol) is charged with THF (10 mL) MeOH (10 mL) and a stirring bar is added. Stirring is initiated. After dissolution, water (5 mL) is added followed by the LiOH (267 mg, 6.36 mmol). After 36 h, tlc analysis (silica, 5% i-PrOH/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 an addition 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 yield 620 mg of amorphous white solid. The sample is purified by column chromatography (silica, 2% to 15% CH3OH in DCM) using an ISCO Companion and a 40 g cartridge. Fractions 14-16 are collected and evaporated by pumping to constant weight gives 380 mg of dry white powder.

Workup

  1. additionis 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 an addition 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

Sources & evidence

ORD record
ord-8f0f3b8e77704f46a0a57089c18acf38
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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