Sodium Hydroxide → [Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid

HRID 479146Notes

Reaction equation

HRID 479146 reaction equation
C([O:3][C:4](=[O:37])[CH:5]([O:35][CH3:36])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[CH3:36][O:35][CH:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[CH:9][CH:8]=1)[C:4]([OH:37])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69556683[Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester

Product 1

HCID 18003560[Rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.143 g of the above prepared [rac]-2-methoxy-3-(4-{3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalen-1-yl)-propionic acid ethyl ester (0.28 mmol) was dissolved in 1.5 ml of THF/EtOH=1/1 and treated with 0.47 ml of 3N NaOH (5 eq.). The reaction mixture was stirred at ambient temperature for 2 h and was then poured onto crashed ice/HCl dil. and extracted twice with AcOEt. The organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness. Crystallization from AcOEt/hexane afforded finally 0.120 g of the title product as white crystals of mp. 67-70°.

Workup

  1. additionwas then poured
  2. extractionextracted twice with AcOEt
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-2016e4ca4fff49f8a137384827e3675c
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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