HCID 57608552, compound → HCID 10162008, compound

HRID 968859Notes

Reaction equation

HRID 968859 reaction equation
C([O:3][C:4](=[O:36])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:22]([CH3:23])[C:21](=[O:24])[N:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)[N:19]=2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C>C(O)C.[OH-].[Na+]>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:20]2[C:21](=[O:24])[N:22]([CH3:23])[C:18]([CH2:17][CH2:16][CH2:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:36])=[O:3])=[CH:14][CH:13]=3)=[N:19]2)=[CH:27][CH:28]=1)([CH3:33])([CH3:34])[CH3:35]

Participants

4

Reactant 1

HCID 57608552HCID 57608552, compound

Product 1

HCID 10162008HCID 10162008, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-(4-{3-[1-(4-t-Butylbenzyl)-4-methyl-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester (0.69 g, 1.39 mmol) was dissolved in ethanol (4 mL)), 1 N NaOH (4.75 mL) was added in one portion and the solution was stirred at ambient temperature overnight. The solution was concentrated to a hazy, colorless oil. This oil was partitioned between 1N HCl (5 mL) and ethyl acetate (5 mL). The aqueous layer was then reextracted with ethyl acetate (5 mL) and the organic layers combined, dried (MgSO4), filtered and concentrated in vacuo at 50° C. to afford the title compound as a clear oil (0.56 g, 86%): 1H NMR (DMSO-d6) δ 12.9 (br s, 1H), 7.31 (d, 2H, J=6 Hz), 7.14 (d, 2H, J=8 Hz), 7.05 (d, 2H, J=7 Hz), 6.73 (d, 2H, J=2 Hz), 4.77 (s, 2H), 3.09 (s, 3H), 2.53 (t, 2H, J=8 Hz), 2.49 (t, 2H, J=8 Hz), 1.81 (quint, 2 H, J=7 Hz), 1.46 (s, 6H), 1.22 (s, 9H); 13C NMR (DMSO-d6) δ 175.8, 154.14, 154.10, 150.5, 147.2, 135.2, 135.0, 129.7, 128.0, 125.9, 119.2, 79.0, 48.3, 34.9, 34.1, 31.8, 27.7, 27.6, 25.7, 25.1; IR (CHCl3) 2966, 1695, 1509, 1235 cm−1; Anal. Calcd. for C27H35N3O4: C, 69.65; H, 7.58; N, 9.02. Found: C, 69.30; H, 7.30; N, 8.96.

Workup

  1. additionwas added in one portion
  2. concentrationThe solution was concentrated to a hazy, colorless oil
  3. customThis oil was partitioned between 1N HCl (5 mL) and ethyl acetate (5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo at 50° C.

Sources & evidence

ORD record
ord-068e2d65a25c4f6b9420a0d200b6210b
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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