Sodium Hydroxide → HCID 9933220, compound

HRID 2215199Notes

Reaction equation

HRID 2215199 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:29][CH:30]([CH3:32])[CH3:31])[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]([CH3:28])([CH3:27])[CH3:26])[O:22][C:23]=2[CH3:24])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.CCO>[C:25]([C:21]1[O:22][C:23]([CH3:24])=[C:19]([CH2:18][CH2:17][O:16][C:10]2[C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:7]([CH2:6][CH:5]([O:29][CH:30]([CH3:31])[CH3:32])[C:4]([OH:33])=[O:3])=[CH:8][CH:9]=2)[N:20]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69487387HCID 69487387, compound

Product 1

HCID 9933220HCID 9933220, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.322 g of the above prepared 3-{4-[2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-2-isopropoxy-propionic acid ethyl ester (0.680 mmol) was dissolved in 3.4 ml of THF/EtOH=1/1, treated with 1.133 ml of 3N NaOH (5 eq.), and kept at ambient temperature for 1.5 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the organic layer washed with water, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/AcOEt afforded finally 0.287 g of the title compound as a white solid of mp. 159–60°.

Workup

  1. additionThe reaction mixture was then poured
  2. washthe organic layer washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customCrystallization from hexane/AcOEt

Sources & evidence

ORD record
ord-1f5241141c994f00a931a6ca36df60d7
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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