Sodium Hydroxide → HCID 12083262, compound

HRID 2229080Notes

Reaction equation

HRID 2229080 reaction equation
C([O:3][C:4](=[O:41])[C:5]([CH3:40])([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]4[S:36][CH:37]=[CH:38][CH:39]=4)[CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[CH3:40][C:5]([O:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]4[S:36][CH:37]=[CH:38][CH:39]=4)[CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:18][CH:19]=1)([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:4]([OH:41])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12083261HCID 12083261, compound

Product 1

HCID 12083262HCID 12083262, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-2-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-3-phenyl-propionic acid ethyl ester (24.7 mmol) was dissolved in methanol (200 mL) and 2N NaOH (150 mL) was added. The resulting cloudy solution became clear after 30 min and the reaction was stirred vigorously overnight. The solution was concentrated under reduced pressure, diluted with H2O (100 mL) and acidified to pH 1 with 5N HCl. The mixture was extracted with ethyl acetate (2×200 mL), dried (MgSO4), and concentrated under reduced pressure to provide an oil. The oil (8.23 g) was recrystallized from ethyl acetate (24 mL) and hexanes (56 mL) to afford 2-Methyl-2-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-3-phenyl-propionic acid as colorless needles after drying at 50° C. under vacuum for 6 h: 1H NMR (400 MHz, CDCl3) δ8.22 (t, 1H, J=1.56 Hz), 7.87 (d, 1H, J=7.82 Hz), 7.66-7.64 (m, 1H), 7.45 (d, 1H, J=7.82 Hz), 7.41-7.40 (m, 1H), 7.31-7.25 (m, 6H), 7.09 (dd, 1H, J=5.08 Hz, J=3.52 Hz), 6.84 (d, 2H, J=9.38 Hz), 6.76 (d, 2H, J=9.38 Hz), 4.17 (t, 2H, J=6.45 Hz), 3.30 (d, 1H, J=13.69 Hz), 3.15 (d, 1H, J=13.69 Hz), 3.01 (t, 2H, J=6.45 Hz), 2.40 (s, 3H), 1.35 (s, 3H); HRMS (ES+) m/z exact mass calculated for C32H30NO5S 540.1857, found 540.1857.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with H2O (100 mL)
  3. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto provide an oil
  7. customThe oil (8.23 g) was recrystallized from ethyl acetate (24 mL) and hexanes (56 mL)

Sources & evidence

ORD record
ord-bd3052484f1248c0ab1e75a6d248f368
Source dataset
uspto-grants-2002_07
Patent number
US06417212B1

Reaction notes

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