Potassium Hydroxide → HCID 10274300, compound

HRID 1935263Notes

Reaction equation

HRID 1935263 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:32])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:5]=1.[OH-].[K+]>C(O)C.O>[CH:14]1([CH2:13][CH:12]([C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:33])=[O:2])=[CH:5][N:6]=2)=[O:32])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67483378HCID 67483378, compound

Product 1

HCID 10274300HCID 10274300, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 30B-b, 102 mg, 0.23 mmol) in ethanol (10 mL) at 25° C. was treated with a solution of potassium hydroxide (40 mg, 0.69 mmol) in water (2.5 mL). This light yellow solution was stirred at 25° C. for 2 h and then concentrated in vacuo to remove ethanol. The resulting aqueous solution was acidified to pH=2 with a 1N aqueous hydrochloric acid solution and then extracted with methylene chloride (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 10/90 hexanes/ethyl acetate plus 1% acetic acid) afforded 6-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-nicotinic acid (74 mg, 76%) as a white solid: FAB-HRMS m/e calcd for C26H26N2O4 (M+H)+ 431.1971, found 431.1987.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove ethanol
  3. extractionextracted with methylene chloride (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-147790305c5b46cdb03ab26a5050bdf3
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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