Hydrochloric Acid → HCID 135992965, compound

HRID 968841Notes

Reaction equation

HRID 968841 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 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 1 h. The solution was cooled to rt and the pH adjusted to 7 with 6N HCl. The solution was concentrated to an oil, which was partitioned between 1N HCl (10 mL) and ethyl acetate (15 mL). The aqueous layer was then reextracted with ethyl acetate (15 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo at 50° C. to afford the title compound as an oil (1.41 g, 97.0%). 1H NMR (DMSO-d6) δ 13.0 (broad s, 1 H), 11.47 (s, 1 H), 7.23 (t, 1 H, J=8 Hz), 7.03 (d, 2 H, J=8 Hz), 6.82 (d, 1 H, J=2 Hz), 6.75 (m, 5 H), 4.73 (s, 2 H), 3.70 (s, 3 H), 3.35 (broad s, 1 H), 2.48 (t, 2 H, J=8 Hz), 2.36 (t, 2 H, J=8 Hz), 1.80 (quint, 2 H, J=7 Hz), 1.46 (s, 6 H); 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 rt
  2. concentrationThe solution was concentrated to an oil, which
  3. customwas partitioned between 1N HCl (10 mL) and ethyl acetate (15 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo at 50° C.

Sources & evidence

ORD record
ord-dedcc6c520a64507909a550dfc87f269
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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