Sodium Hydroxide → 2-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acid

HRID 1297595Notes

Reaction equation

HRID 1297595 reaction equation
C[O:2][C:3](=[O:33])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]([C:17]2[C:18]([O:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+]>C(O)(C)(C)C>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([O:23][C:18]3[C:17]([C:15]([NH:14][CH2:13][C:10]4[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:33])=[O:2])=[CH:8][CH:9]=4)=[O:16])=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:25][C:26]=2[O:30][CH2:29]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 101822602-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acid methyl ester

Product 1

HCID 98242372-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-2-methyl-propionic acid methyl ester (0.451 g) was suspended in tertiary butanol (30 mL). Sodium hydroxide (1.68 mL of a 6N aqueous solution) was added to the suspension, and the reaction mixture was heated to reflux. After 1 hour the reaction mixture was cooled to ambient temperature, the solvent removed in vacuo, water added (20 mL), and the pH adjusted from to 3 with concentrated hydrochloric acid. The solution was subsequently extracted with ethyl acetate (7×50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield the crude product (0.490 g). The crude product was purified by silica gel chromatography (acetic acid:methanol:dichloromethane=1:10:89) to yield pure title compound (0.409 g).

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. customthe solvent removed in vacuo, water
  3. additionadded (20 mL)
  4. extractionThe solution was subsequently extracted with ethyl acetate (7×50 mL)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield the crude product (0.490 g)
  9. customThe crude product was purified by silica gel chromatography (acetic acid:methanol:dichloromethane=1:10:89)

Sources & evidence

ORD record
ord-30d22ee5c10741a2bd780031a62c0a66
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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