Sodium Hydroxide → 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

HRID 1683988Notes

Reaction equation

HRID 1683988 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:26])[CH2:20][C:21]([O:23]CC)=[O:22])=[C:8]2[CH3:27])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:26])[CH2:20][C:21]([OH:23])=[O:22])=[C:8]2[CH3:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19041640HCID 19041640, compound

Product 1

HCID 98673334-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ester from Step 5 (3.5 g, 7.6 mmol) in MeOH/THF (50 mL/35 mL) was added 1M NaOH (22.9 mL, 22.9 mmol). After heating at reflux for 2 h, the mixture was concentrated under vacuum and the residue was partitioned between EtOAc/H2O containing HOAc (3 mL). The organic layer was washed with H2O, brine, and was then dried (MgSO4), filtered, and evaporated. The resulting solid was stirred vigorously with 1:10 EtOAc/hexane for 2 h to give, after filtration, 2.81 g of white solid.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. concentrationthe mixture was concentrated under vacuum
  4. customthe residue was partitioned between EtOAc/H2O
  5. additioncontaining HOAc (3 mL)
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialwas then dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give
  11. filtrationafter filtration, 2.81 g of white solid

Sources & evidence

ORD record
ord-ac7eb8223d4b4f35881e2520adcd1d84
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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