Tetrahydrofuran → HCID 608124, compound

HRID 1775429Notes

Reaction equation

HRID 1775429 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:18]([O:20]CC)=[O:19])(=[O:3])[CH3:2].O1CCCC1.[OH-].[Na+]>C(O)C>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:18]([OH:20])=[O:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 44581689HCID 44581689, compound

Product 1

HCID 608124HCID 608124, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-(2-acetamidoethyl)-5-methoxy-1H-indole-2-carboxylate (350 mg), tetrahydrofuran (5.00 mL), and ethanol (5.00 mL) was added a 1 M aqueous sodium hydroxide solution (2.00 mL), followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the obtained residue was dissolved in water and adjusted to be weakly acidic by the addition of 1 M hydrochloric acid. The precipitated solid was collected by filtration and then dried to obtain 3-(2-acetamidoethyl)-5-methoxy-1H-indole-2-carboxylic acid (300 mg) as a gray solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in water
  3. additionto be weakly acidic by the addition of 1 M hydrochloric acid
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-76d2c7079c5b496b956e283a590c3fe9
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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