Hydrochloric Acid → HCID 135992965, compound

HRID 968826Notes

Reaction equation

HRID 968826 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][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[N:19]=2)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].Cl>C(O)C.O>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:20]1[C:21](=[O:23])[NH:22][C:18]([CH2:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:33])=[O:3])=[CH:14][CH:13]=2)=[N:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 135992966HCID 135992966, compound

Product 1

HCID 135992965HCID 135992965, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-(4-{3-[1-(3-Methoxy-benzyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester (1.55 g, 3.42 mmol) was dissolved in a mixture of ethanol (7.5 mL) and deionized water (7.5 mL). Solid sodium hydroxide (0.36 g, 8.73 mmol) was added in one portion and the solution was warmed to 70° C. and stirred for one hour. The solution was cooled to ambient temperature and the pH adjusted to 7 with 6N HCl. The solution was concentrated to a hazy yellow oil. This oil was partitioned between 1N HCl (10 mL) and ethyl acetate (15 mL). The aqueous layer was then re-extracted with ethyl acetate (15 mL) and the organic layers combined, dried (MgSO4), filtered and concentrated in vacuo at 50° C. overnight to afford the title compound as a clear oil (1.41 g, 97.0%). 1H NMR (DMSO-d6) δ 13.0 (broad s, 1H), 11.47 (s, 1H), 7.23 (t, 1H, J=8 Hz), 7.03 (d, 2H, J=8 Hz), 6.82 (d, 1H, J=2 Hz), 6.75 (m, 5H), 4.73 (s, 2H), 3.70 (s, 3H), 3.35 (broad s, 1H), 2.48 (t, 2H, J=8 Hz), 2.36 (t, 2H, J=8 Hz), 1.80 (quint, 2H, J=7 Hz), 1.46 (s, 6H); 13C NMR (DMSO-d6, 20° C.) δ 175.8, 160.0, 155.0, 154.1, 146.8, 139.8, 135.0, 130.3, 129.7, 120.1, 119.1, 113.8, 113.2, 78.9, 55.6, 47.8, 40.6, 40.5, 34.0, 28.4, 27.5, 26.2, 25.7; IR (CHCl3) 1707, 1603, 1509, 1159 cm−1; Anal. Calcd. for C23H27N3O5: C, 64.93; H, 6.40; N, 9.88. Found: C, 65.02; H, 6.65; N, 9.57.

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. concentrationThe solution was concentrated to a hazy yellow oil
  3. customThis oil was partitioned between 1N HCl (10 mL) and ethyl acetate (15 mL)
  4. extractionThe aqueous layer was then re-extracted with ethyl acetate (15 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-3819c6c874b948cf8b83ccff8432e0d9
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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