Sodium Hydroxide → HCID 25174150, compound

HRID 420350Notes

Reaction equation

HRID 420350 reaction equation
C([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:25]=[C:24]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH:23]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44]CC)=[O:43])C.[OH-].[Na+]>C(O)C>[C:42]([CH2:41][CH2:40][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)[CH:25]=[C:24]([C:34]3[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=3)[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:47])=[O:3])([OH:44])=[O:43]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57586506HCID 57586506, compound

Product 1

HCID 25174150HCID 25174150, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
52.5 °C

Procedure

To a solution of 4-{3-[6-(3,5-di-pyridin-4-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (195 mg, 0.3 mmol) in ethanol (10 mL) was added aqueous 1.0 N sodium hydroxide (8 mL) at room temperature. The mixture was heated to 50-55° C. and the resulting solution was stirred for 3 h. Then, the reaction mixture was concentrated and the residue was diluted with water (20 mL) and extracted with diethyl ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1 N hydrochloric acid until the solution become slightly acidic. The resulting white solids were collected by filtration and washed with water. After air-drying, 4-{2-(2-carboxy-ethyl)-3-[6-(3,5-di-pyridin-4-yl-phenoxy)-hexyl]-phenoxy}-butyric acid (176 mg, 99%) was isolated as a white solid: ES(+)-HRMS m/e calculated for C35H38N2O6 (M+H)+ 583.2803, found 584.2805.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. additionthe residue was diluted with water (20 mL)
  3. extractionextracted with diethyl ether (50 mL)
  4. customto remove any neutral impurities
  5. filtrationThe resulting white solids were collected by filtration
  6. washwashed with water
  7. customAfter air-drying

Sources & evidence

ORD record
ord-5cad0b2889b54b7e88a42ffed1fd87d1
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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