Sodium Hydroxide → HCID 135992963, compound

HRID 968856Notes

Reaction equation

HRID 968856 reaction equation
C([O:3][C:4](=[O:33])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]2[NH:22][C:21](=[O:23])[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=3)[N:19]=2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[CH3:32][C:27]1[CH:26]=[C:25]([CH2:24][N:20]2[C:21](=[O:23])[NH:22][C:18]([CH2:17][CH2:16][CH2:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:33])=[O:3])=[CH:14][CH:13]=3)=[N:19]2)[CH:30]=[CH:29][C:28]=1[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136368693HCID 136368693, compound

Product 1

HCID 135992963HCID 135992963, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-{3-[1-(3,4-Dimethylphenylmethyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methylpropionic acid ethyl ester (916 mg, 1.97 mmol) was dissolved in ethanol (10 mL) and 2N NaOH (3.0 mL, 6.0 mmol) was added in one portion. The solution was stirred at room temperature for one hour, then concentrated to a hazy colorless oil. This oil was partitioned between 1N HCl (10 mL) and ethyl acetate (10 mL). The aqueous layer was then reextracted with ethyl acetate (10 mL). Solids precipitated from this solution on stirring. The slurry was cooled to 0° C., filtered and dried in vacuo at 50° C. overnight to afford the title compound as a white solid (695 mg, 80%): mp 145.8-149.6° C.; 1H-NMR (DMSO-d6) δ 12.98 (s, 1H), 7.05 (dd, 3H, J=8.5, 3.0 Hz), 7.00 (s, 1H), 6.93 (d, 1H, J=7.5 Hz), 6.73 (d, 2H, J=8.5 Hz), 4.73 (s, 2H), 2.52 (t, 2H, J=7.5 Hz), 2.47 (t, 2H, J=7.5 Hz), 2.14 (s, 6H), 1.80 (quint, 2H, J=7.5 Hz), 1.46 (s, 6H); 13C NMR (DMSO-d6, 20° C.) δ 175.8, 154.1, 154.0, 147.1, 136.8, 135.9, 135.3, 135.2, 130.1, 129.7, 129.4, 125.7, 119.2, 78.9, 48.4, 34.1, 27.7, 27.6, 25.7, 25.1, 20.0, 19.7; IR (CHCl3) 2936, 2490, 1730, 1658, 1510, 1148 cm−1; Anal. Calcd. for C25H31N3O4: C, 68.63; H, 7.14; N, 9.60. Found: C, 68.23; H, 7.01; N, 9.44.

Workup

  1. concentrationconcentrated to a hazy colorless oil
  2. customThis oil was partitioned between 1N HCl (10 mL) and ethyl acetate (10 mL)
  3. customSolids precipitated from this solution
  4. stirringon stirring
  5. temperatureThe slurry was cooled to 0° C.
  6. filtrationfiltered
  7. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-33f9fbb1b1bf45ef995bc804b0c9b9db
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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