Lithium hydroxide, monohydrate → 3-Methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoic acid

HRID 1975420Notes

Reaction equation

HRID 1975420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23](=[O:33])[NH:24][CH2:25][CH:26]([CH3:32])[CH2:27][C:28]([F:31])([F:30])[F:29])[CH:21]=2)[N:16]([CH3:34])[CH:15]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+]>CO.O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23](=[O:33])[NH:24][CH2:25][CH:26]([CH3:32])[CH2:27][C:28]([F:30])([F:29])[F:31])[CH:21]=2)[N:16]([CH3:34])[CH:15]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10005193HCID 10005193, compound

Product 1

HCID 100499743-Methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoic acidYield 88.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoate (0.64 g) in methanol (3.5 mL), tetrahydrofuran (3.5 mL) and water (1.3 mL) was treated with lithium hydroxide monohydrate (0.34 g). The mixture was stirred for 18 hours and the organic solvents evaporated. The resulting aqueous solution was acidified with 10% (w/v) hydrochloric acid. The white precipitate which formed was collected by filtration, washed with water and dried under vacuum to give 3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoic acid as a white powder (0.55 g, 88%); partial NMR (300 MHz, DMSO-d6): 1.00 (d, 3H, CHCH3) 3.21 (m, 2H, NCH2), 3.76 (s, 3H, NCH3), 3.91 (s, 3H, OCH3), 4.07 (s, 2H, CH2), 7.15 (m, 2H, ArH), 7.46 (m, 3H, ArH), 7.68 (dd, 1H, ArH), 8.10 (d, 1H, ArH), 8.44 (t, 1H, NHCO).

Workup

  1. customthe organic solvents evaporated
  2. customThe white precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b9eee883f18f46a4a81d53387ebd8f69
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

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