Sodium Hydroxide → HCID 57709172, compound

HRID 547035Notes

Reaction equation

HRID 547035 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([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:9][CH:8]=1.[Cl-].[NH4+]>CO>[CH2:20]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]([OH:42])=[O:4])=[CH:12][CH:11]=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])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)=[C:24]([CH3:38])[CH:23]=1)[CH2:39][CH3:40])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 67065212HCID 67065212, compound

Product 1

HCID 57709172HCID 57709172, compoundYield 58.7%

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 [4′-(1-ethyl-1-{4-[2-(1-hydroxy-cycloheptyl)-(E)-vinyl]-3-methyl-phenyl}-propyl)-2′-methyl-biphenyl-4-yl]-acetic acid methyl ester (14.0 mg) in methanol (1.0 mL), and the mixture was stirred with microwave heating at 100° C. for five minutes. An ammonium chloride 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 silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10) to give the target compound as a colorless oil (8.0 mg, 19% 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 silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10)

Sources & evidence

ORD record
ord-3bc3e5bab32c4f6b961f50faf187ff02
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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