Sodium Hydroxide → HCID 18003589, compound

HRID 479138Notes

Reaction equation

HRID 479138 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([O:33][CH3:34])[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]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[Cl:32][C:27]1[CH:26]=[C:25]([C:21]2[O:22][C:23]([CH3:24])=[C:19]([CH2:18][CH2:17][O:16][C:10]3[C:11]4[CH:15]=[CH:14][S:13][C:12]=4[C:7]([CH2:6][CH:5]([O:33][CH3:34])[C:4]([OH:35])=[O:3])=[CH:8][CH:9]=3)[N:20]=2)[CH:30]=[C:29]([Cl:31])[CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69557038HCID 69557038, compound

Product 1

HCID 18003589HCID 18003589, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.142 g of the above prepared [rac]-3-(4-{2-[2-(3,5-dichloro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-2-methoxy-propionic acid ethyl ester (0.27 mmol) was dissolved in 4 ml of THF/EtOH=1/1 and treated with 0.68 ml of 1N NaOH (2.5 eq.). The reaction mixture was stirred at ambient temperature and progress of the hydrolysis followed by TLC. After 2 h, the reaction mixture was poured onto crashed ice/HCl dil. and extracted twice with AcOEt. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Crystallization from AcOEt/hexane yielded finally 0.107 g of the title product as white crystals of mp. 160-61°.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with AcOEt
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-3a810aa4fbbe4edebe537f86974cc0dc
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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