Water → 2-(4-Benzyloxy-phenyl)-3-cyclopentyl-propionic acid

HRID 1935220Notes

Reaction equation

HRID 1935220 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].O>O1CCCC1.O.CO>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:25])=[O:2])=[CH:16][CH:15]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 674831552-(4-Benzyloxy-phenyl)-3-cyclopentyl-propionic acid methyl ester

Product 1

HCID 224679042-(4-Benzyloxy-phenyl)-3-cyclopentyl-propionic acidYield 60.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-benzyloxy-phenyl)-3-cyclopentyl-propionic acid methyl ester (1.38 g, 4.08 mmol) in tetrahydrofuran/water/methanol (10.2 ml, 3:1:1) was treated with a 2N aqueous sodium hydroxide solution (3.06 mL, 6.12 mmol). The reaction was stirred at 25° C. for 16 h. At this time, an additional amount of the 2N aqueous sodium hydroxide solution (3.06 mL, 6.12 mmol) was added. The reaction was stirred at 25° C. for an additional 24 h. At this time, the reaction mixture was poured into water and extracted into methylene chloride. The layers were separated. The aqueous layer was acidified to pH=1 with a 1N aqueous hydrochloric acid solution and was then extracted with a solution of methylene chloride/methano (90/10). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(4-benzyloxy-phenyl)-3-cyclopentyl-propionic acid (0.79 g, 60.2%) as a white solid: mp 112-114° C.

Workup

  1. stirringThe reaction was stirred at 25° C. for an additional 24 h
  2. extractionextracted into methylene chloride
  3. customThe layers were separated
  4. extractionwas then extracted with a solution of methylene chloride/methano (90/10)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1924d089a48c493f90a77158de1f36fc
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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