HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1741904
Notes
Print preview

Reaction equation

HRID 1741904 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

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-48dd9c06ca844426a80d05d4d3d0fe5b
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05334765

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes