Water → HCID 21349860, compound

HRID 2186754Notes

Reaction equation

HRID 2186754 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][CH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]([O:27]C)=[O:26])[C:17]=2[O:16][CH2:15]1.[OH-].[Na+].O>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][CH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]([OH:27])=[O:26])[C:17]=2[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21349899HCID 21349899, compound

Product 1

HCID 21349860HCID 21349860, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (+)-3-(2-(3-(2-hydroxyphenyl)propylthio)ethyl)-2,3-dihydrobenzofuran-7-yloxyacetate (160 mg) was dissolved in methanol (4 ml), and a 2N sodium hydroxide aqueous solution (0.4 ml) was added to the resultant solution, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into water and then extracted with ethyl acetate twice. The combined organic layers were washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was filtered off, and the filtrate was concentrated. The residue was purified by Lober® column DIOL (elution solvent: hexane/ethyl acetate=1/2) to obtain (+)-3-(2-(3-(2-hydroxyphenyl)propylthio)ethyl)-2,3-dihydrobenzofuran-7-yloxyacetic acid (145 mg). This product was dissolved in chloroform, and diethanolamine was added to the resultant solution. The solvent was distilled off under reduced pressure, and the residue was recrystallized from hexane/ethanol to obtain the object compound (140 mg, yield 76%).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationSodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by Lober® column DIOL (elution solvent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-a9f3456c446c42baaf84b2717a946cb3
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

Loading…