Sodium Hydroxide → HCID 22339950, compound

HRID 1393474Notes

Reaction equation

HRID 1393474 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[N:6]=[C:7]([C:11]2[S:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[O:8][C:9]=1[CH3:10].[OH-].[Na+]>CO>[CH3:10][C:9]1[O:8][C:7]([C:11]2[S:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[N:6][C:5]=1[CH2:4][C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69316030HCID 69316030, compound

Product 1

HCID 22339950HCID 22339950, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

[5-Methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-acetic acid methyl ester (3.44 g, 13.7 mmol), in MeOH (45 mL) was treated with 5N NaOH (16 mL) and then the solution was warmed to 40° C. After 30 min, the reaction mixture was concentrated under reduced pressure, suspended in water, and then acidified to pH=1 with 5N HCl. The mixture was extracted with EtOAc (2×), dried (MgSO4), and concentrated to provide 2.47 g (76%) of the product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=3.6 Hz, 1H), 6.73 (dd, J=3.6, 0.8 Hz, 1H), 3.59 (s, 2H), 2.51 (s, 3H), 2.32 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b718677477c346aa8da50d66607d8535
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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