Sodium Hydroxide → 4-Methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}benzoic acid

HRID 644012Notes

Reaction equation

HRID 644012 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][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]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:16][CH:15]=1.[OH-].[Na+]>O1CCOCC1>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:35])=[O:2])=[C:5]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:18][CH:19]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 587911484-Methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-benzoic acid methyl ester

Product 1

HCID 115254194-Methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title D compound, 4-methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-benzoic acid methyl ester (220 mg, 0.46 mmol) is taken up in 5 mL of 1,4-dioxane and 1.4 mL of 1 N aqueous NaOH is added. The solution is stirred overnight at RT, followed by 5 h at 90° C. The mixture is concentrated under vacuum, and the residue is acidified (4 N HCl) and extracted with EtOAc. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated to give 4-methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}benzoic acid: m.p. 113-115° C.; ESI-MS 460 [M+1]+.

Workup

  1. waitfollowed by 5 h at 90° C
  2. concentrationThe mixture is concentrated under vacuum
  3. extractionextracted with EtOAc
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d1030230b5d44369ad9addaf4caccb38
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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