Sodium Hydroxide → HCID 57463799, compound

HRID 547091Notes

Reaction equation

HRID 547091 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:39][CH3:40])([C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]4([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:24]([CH3:38])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:41])[CH:12]=1.C(=O)(O)[O-].[Na+]>CO>[CH2:20]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:12]=[C:7]([CH2:6][C:5]([OH:42])=[O:4])[CH:8]=[N:9][CH:10]=2)=[C:14]([CH3:41])[CH:15]=1)([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:24]([CH3:38])[CH:23]=1)[CH2:39][CH3:40])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 57463800HCID 57463800, compound

Product 1

HCID 57463799HCID 57463799, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A 2 N sodium hydroxide aqueous solution (0.50 mL, 1.0 mmol) was added to a solution of the mixture containing {5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cycloheptyl)-(E)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic acid methyl ester (65.3 mg) in methanol (1.0 mL), and the mixture was stirred with microwave heating at 100° C. for five minutes. A sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate and washing with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (Shiseido CAPCELL PAK C18 MGII, 20 mm I.D.×50 mm, methanol:20 mM ammonium acetate solution=55:45 to 100:0, 20 mL/min). A sodium bicarbonate solution was added to the eluate, followed by extraction with ethyl acetate and washing with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the target compound as a colorless oil (16.0 mg, 30% in two steps).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by high performance liquid chromatography (Shiseido CAPCELL PAK C18 MGII, 20 mm I.D.×50 mm, methanol:20 mM ammonium acetate solution=55:45 to 100:0, 20 mL/min)
  7. additionA sodium bicarbonate solution was added to the eluate
  8. extractionfollowed by extraction with ethyl acetate
  9. washwashing with brine
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33355d03de134d6081e409b95634e218
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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