Potassium Hydroxide → 4-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 2079831Notes

Reaction equation

HRID 2079831 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([O:27]C)=[O:26])([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.[OH-].[K+]>O.CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:14])([F:16])[F:15])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([OH:27])=[O:26])([CH2:21][CH2:22]1)[CH2:19][CH2:18]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20755116Methyl 4-(4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 592555694-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of methyl ester 1-C (1.19 g, 3.0 mmol) in 5% H2O/MeOH (30 ml) was treated with KOH (0.51 g, 9.1 mmol) at 60° C. under a nitrogen atmosphere for 18 h. The resulting mixture was concentrated, diluted with water (150 ml), washed with EtOAc and acidified with aqueous HCl (1 N) to pH=3. The precipitate was filtered, washed with a small amount of water and ether and dried under vacuum to yield 1-D as a pink solid. MS (ESI+)=380.18; 1H NMR (500 MHz, CD3OD): δ 7.95-7.93 (m, 1 H), 7.86-7.82 (m, 2 H), 7.61-7.59 (m, 1 H), 3.53 (s, 3 H), 2.15 (m, 6 H), 2.02-1.96 (m, 6 H) ppm.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with water (150 ml)
  3. washwashed with EtOAc
  4. filtrationThe precipitate was filtered
  5. washwashed with a small amount of water and ether
  6. customdried under vacuum
  7. customto yield 1-D as a pink solid

Sources & evidence

ORD record
ord-09b1e76c9fee4c02b6ebd8373166e3d0
Source dataset
uspto-grants-2011_04
Patent number
US07932280B2

Reaction notes

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