Sodium Hydroxide → 2-Methoxy-3-(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)benzo[b]thiophen-7-yl)propanoic acid

HRID 479118Notes

Reaction equation

HRID 479118 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:31][CH3:32])[CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CO>[CH3:32][O:31][CH:5]([CH2:6][C:7]1[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)[C:4]([OH:33])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69557272HCID 69557272, compound

Product 1

HCID 99109512-Methoxy-3-(4-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)benzo[b]thiophen-7-yl)propanoic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.184 g of 2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester (0.40 mmol) was dissolved in 1 ml of THF/MeOH=1/1 and treated with 0.670 ml of 3N NaOH. The reaction mixture was kept over night at RT and then quenched by pouring onto crashed ice/HCl. Twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left a crude product, which was purified by crystallisation from AcOEt/hexane to yield 0.158 g of the title compound as white solid, mp.121-122°.

Workup

  1. waitThe reaction mixture was kept over night at RT
  2. customquenched
  3. additionby pouring
  4. extractionTwofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. waitleft a crude product, which
  8. customwas purified by crystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-33f4d6c44454418d90082c9e964a7e44
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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