Sodium Hydroxide → 2-Methyl-3-(4-{2-[5-methyl-2-(3-thiophen-3-ylphenyl)oxazol-4-yl]ethoxy}phenyl)-2-phenoxypropionic acid

HRID 348284Notes

Reaction equation

HRID 348284 reaction equation
C([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[CH:32]=[CH:31][S:30][CH:29]=4)[CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[CH3:40][C:5]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[CH:32]=[CH:31][S:30][CH:29]=4)[CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:11][CH:12]=1)[C:4]([OH:41])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 693540362-Methyl-3-(4-{2-[5-methyl-2-(3-thiophen-3-ylphenyl)oxazol-4-yl]ethoxy}phenyl)-2-phenoxypropionic acid ethyl ester

Product 1

HCID 102305812-Methyl-3-(4-{2-[5-methyl-2-(3-thiophen-3-ylphenyl)oxazol-4-yl]ethoxy}phenyl)-2-phenoxypropionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

2-Methyl-3-(4-{2-[5-methyl-2-(3-thiophen-3-ylphenyl)oxazol-4-yl]ethoxy}phenyl)-2-phenoxypropionic acid ethyl ester (3.6 mmol) in MeOH (7 mL) was treated with 2N NaOH (7 mL) and warmed to 55° C. After 18 h, the mixture was concentrated under reduced pressure and then acidified with 5N HCl to pH=1. The solution was extracted with EtOAc and then the organic phases dried (Na2SO4), filtered and concentrated to a white solid. 1H NMR (400 MHz, DMSO-d6) δ8.15 (t, J=1.6 Hz, 1H), 7.98 (dd, J=2.8 Hz, J=1.6 Hz, 1H), 7.82–7.79 (m, 2H), 7.66 (dd, J=7.6 Hz, J=2.8 Hz, 1H), 7.59 (dd, J=6.4 Hz, J=1.2 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 7.24 (t, J=8.0 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 6.93 (t, J=7.6 Hz, 1H), 6.85 (d, J=8.4 Hz, 1H), 6.79 (dd, J=7.6 Hz, J=1.2 Hz, 2H), 4.19 (t, J=6.4 Hz, 2H), 3.16 (d, J=13.2 Hz, 1H), 3.04 (d, J=13.2 Hz, 1H), 2.92 (t, J=6.4 Hz, 2H), 2.36 (s, 3H), 1.26 (s, 3H); MS (EI) 540.2 (M+H)+, 538.3 (M−M)−.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialthe organic phases dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-346cc069f7a3466e9f24af022d1fd0a8
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

Loading…