Lithium Hydroxide → 2-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid

HRID 1008300Notes

Reaction equation

HRID 1008300 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([OH:28])[C:25]([C:29]3[N:30]=[CH:31][O:32][CH:33]=3)=[CH:24][C:23]=2[CH2:34][CH3:35])[C:12]=1[CH2:36][CH2:37][CH3:38].[OH-].[Li+]>CO>[CH2:34]([C:23]1[CH:24]=[C:25]([C:29]2[N:30]=[CH:31][O:32][CH:33]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:36][CH2:37][CH3:38])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:39])=[O:2])[CH3:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 601163952-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 98066212-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-{3-[3-(2-ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (89 mg, 0.14 mmol) in methanol (2 mL) was added 1 M lithium hydroxide solution (0.28 mL) and the resulting mixture warmed at 60° C. for 3.5 h. The mixture was cooled to room temperature and concentrated in vacuo. The aqueous residue was diluted with water and the pH adjusted to ˜4. The mixture was extracted three times with methylene chloride. The combined organic extracts were dried (sodium sulfate), filtered, and concentrated in vacuo to provide 27 mg (92%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 12.83 (bs, 1H), 10.12 (bs, 1H), 8.39 (s, 1H), 8.25 (s, 1H), 7.78 (dd, J=8, 1 Hz, 1H), 7.64 (s, 1H), 7.47 (t, J=8 Hz, 1H), 7.16 (m, 2H), 6.80 (t, J=8 Hz, 2H), 6.56 (s, 1H), 6.35 (d, J=8 Hz, 1H), 4.20 (t, J=6 Hz, 2H), 4.12 (t, J=6 Hz, 2H); 2.54 (m, 4H), 2.24 (quintet, J=6 Hz, 2H), 1.43 (hextet, J=8 Hz, 2H), 1.10 (t, J=8 Hz, 3H), 5 0.80 (t, J=8 Hz, 3H); TOF MS ES+ exact mass calculated for C30H32NO7 (p+1): m/z=518.2179. Found: 518.2206; IR (KBr, cm−1) 2961, 1696, 1460, 1222. Anal. Calcd for C30H31NO7: C, 69.62; H, 6.04; N, 2.71. Found: C, 68.71; H. 5.82; N, 2.65.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe aqueous residue was diluted with water
  4. extractionThe mixture was extracted three times with methylene chloride
  5. dry with materialThe combined organic extracts were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6864c9959f814ce59e83fe421c049680
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

Loading…