Sodium Hydroxide → HCID 19711377, compound

HRID 725033Notes

Reaction equation

HRID 725033 reaction equation
C[O:2][C:3]([CH:5]([CH3:29])[CH2:6][C:7]1[CH:8]=[C:9]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:10]=[C:11]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=1)=[O:4].[OH-].[Na+]>O1CCOCC1>[C:3]([CH:5]([CH3:29])[CH2:6][C:7]1[CH:8]=[C:9]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:10]=[C:11]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19711370HCID 19711370, compound

Product 1

HCID 19711377HCID 19711377, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of t-butyl 3-[3-(2-methoxycarbonyl-1-propyl)-5-(3-pyridylmethyl)phenyl]propanoate (Preparation 28; 2.84 g), 2N aqueous sodium hydroxide solution (4.3 ml) and 1,4-dioxane (13 ml) was stirred at room temperature for 2 hours, heated at 100° C. for 1.5 hours and then allowed to stand at room temperature for a further 18 hours. The solvent was evaporated under vacuum and the residue partitioned between ethyl acetate and water. The aqueous phase was separated, acidified with glacial acetic acid and extracted twice with dichloromethane, then the combined organic solutions dried (MgSO4) and evaporated under vacuum. The residue was chromatographed on silica gel using a dichloromethane in methanol elution gradient (0 to 7% methanol), and the product fractions combined and evaporated under vacuum to give the title compound as a gum (1.88 g); Rf 0.60 (SS 7). Found: C, 71.72; H, 7.60; N, 3.75. C23H29NO4 requires C, 72.03; H, 7.62; N, 3.65%.

Workup

  1. temperatureheated at 100° C. for 1.5 hours
  2. waitto stand at room temperature for a further 18 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue partitioned between ethyl acetate and water
  5. customThe aqueous phase was separated
  6. extractionextracted twice with dichloromethane
  7. dry with materialthe combined organic solutions dried (MgSO4)
  8. customevaporated under vacuum
  9. customThe residue was chromatographed on silica gel using
  10. washa dichloromethane in methanol elution gradient (0 to 7% methanol)
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-ae356aab5eb24744896741392c40db6f
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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