Sodium Hydroxide → HCID 11058026, compound

HRID 1609907Notes

Reaction equation

HRID 1609907 reaction equation
C([O:3][C:4](=[O:30])[C:5]([CH3:29])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+]>CO>[CH3:29][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:30])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11025958HCID 11025958, compound

Product 1

HCID 11058026HCID 11058026, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid ethyl ester (6.4 g, 15.6 mmol) was dissolved in MeOH (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 EtOAc (2×200 mL), dried (MgSO4), and concentrated under reduced pressure to provide a white solid. The compound was recrystallized from CH3CN (85 mL) to afford the product (4.50 g, 75%) as colorless needles after drying at 50° C. under vacuum for 6 h: Rf=0.14 in 35% EtOAc/hexanes; mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 7.98-7.96 (m, 2H), 7.44-7.41 (m, 3H), 6.91-6.79 (m, 4H), 4.16 (t, J=8.8 Hz, 2H), 2.99 (t, J=8.8 Hz, 2H), 2.38 (s, 3H), 1.53 (s, 6H); 13C (100 MHz, CDCl3) δ 177.2, 159.7, 154.7, 148.3, 145.3, 132.4, 130.1, 128.7, 127.2, 126.1, 122.1, 114.9, 79.9, 67.0, 26.1, 25.1, 10.2; IR (CHCl3) 2991, 1775, 1718, 1554, 1506, 1469, 1237, 1145, 1023 cm−1; HRMS (TOF) m/e calcd. for C22H24NO5 (M++1) 382.1654, found 382.1628.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted with H2O (100 mL)
  3. extractionThe mixture was extracted with EtOAc (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto provide a white solid
  7. customThe compound was recrystallized from CH3CN (85 mL)

Sources & evidence

ORD record
ord-d0752117ac0e42e0ad74d1dead3acace
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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