Sodium Hydroxide → HCID 136368716, compound

HRID 968851Notes

Reaction equation

HRID 968851 reaction equation
C([O:3][C:4](=[O:31])[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][CH:28]=[CH:27][CH:26]=3)[N:19]=2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>C(O)C>[C:25]1([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:31])=[O:3])=[CH:14][CH:13]=3)=[N:19]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136368717HCID 136368717, compound

Product 1

HCID 136368716HCID 136368716, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-{3-[1-(Phenylmethyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methylpropionic acid ethyl ester (557 mg, 1.20 mmol) was dissolved in ethanol (5 mL) and 1N aq. NaOH (3.6 mL, 3.6 mmol) was added in one portion and the solution was stirred at room temperature for 16 h. The solution was then concentrated to a hazy colorless oil. This oil was diluted with water (5 mL) and washed with t-butyl methyl ether (5 mL). The pH of the aqueous layer was adjusted to <1with conc. HCl and the aqueous was extracted with ethyl acetate (10 mL, then 5 mL). This solution was washed with 1 N aqueous HCl (5 mL) and sat'd aq. NaCl (5 mL), dried (MgSO4), and concentrated in vacuo to afford the title compound as a clear colorless oil (442 mg, 84.5%). 1H NMR (DMSO-d6) δ 12.9 (br s, 1H), 7.30 (t, 2H, J=7 Hz), 7.25 (d, 1H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 7.04 (d, 2H J=8 Hz), 6.72 (d, 2H, J=8 Hz), 4.83 (s, 2H), 3.47 (t, 2H, J=7 Hz), 2.54 (t, 2H, J=8 Hz), 2.49 (t, 2H, J=8 Hz), 1.83 (quint, 2H, J=7 Hz), 1.53, (m, 2H), 1.46 (s, 6H), 0.80 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 175.8, 154.1, 146.0, 138.1, 135.2, 129.7, 129.2, 128.0, 119.3, 79.0, 48.5, 42.8, 34.0, 27.9, 25.7, 24.8, 22.5, 11.5; IR (CHCl3) 2938, 1509, 1468, 1233, 1155 cm−1; Anal. Calcd. For C25H31N3O4: C, 68.63; H, 7.14; N, 9.60. Found: C, 68.24; H, 6.95; N, 9.40.

Workup

  1. concentrationThe solution was then concentrated to a hazy colorless oil
  2. additionThis oil was diluted with water (5 mL)
  3. washwashed with t-butyl methyl ether (5 mL)
  4. extractionthe aqueous was extracted with ethyl acetate (10 mL
  5. washThis solution was washed with 1 N aqueous HCl (5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e03531c81807496cb88cbc67c35bdd61
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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