Hydrochloric Acid → 4-[6-(2-Ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoic acid

HRID 1904460Notes

Reaction equation

HRID 1904460 reaction equation
[CH2:1]([CH:3]([CH2:29][CH2:30][CH2:31][CH3:32])[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:9][CH:8]=1)=[O:5])[CH3:2].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH2:1]([CH:3]([CH2:29][CH2:30][CH2:31][CH3:32])[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 20038737Methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoate

Product 1

HCID 147087144-[6-(2-Ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoic acidYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of ester (C) (0.7 g), lithium hydroxide hydrate (0.41 g), tetrahydrofuran (4 ml), methanol (4 ml), and water (1.6 ml) was stirred overnight. The mixture was then evaporated. The white solid obtained was dissolved in water (50 ml). Acidification of this homogeneous alkaline solution by dropwise addition of 10% v/v hydrochloric acid gave a fine white precipitate which was recrystallized from ethyl acetate (40 ml) to give 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoic acid (D) (0.13 g; 30%) as a solid; mp 234°-235° C.

Workup

  1. customThe mixture was then evaporated
  2. customThe white solid obtained
  3. customgave a fine white precipitate which
  4. customwas recrystallized from ethyl acetate (40 ml)

Sources & evidence

ORD record
ord-fc225e55c282413dbf6be7719c277703
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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