HCID 22865619, compound → HCID 15388997, compound

HRID 743995Notes

Reaction equation

HRID 743995 reaction equation
C[O:2][C:3](=[O:43])/[C:4](/[CH2:33][C:34]1[CH:39]=[CH:38][C:37]2[O:40][CH2:41][O:42][C:36]=2[CH:35]=1)=[C:5](/[C:23]1[N:27]([CH3:28])[C:26]([CH2:29][CH2:30][CH2:31][CH3:32])=[N:25][CH:24]=1)\[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17]>[OH-].[Na+].C(O)(C)C>[CH2:29]([C:26]1[N:27]([CH3:28])[C:23](/[C:5](/[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=2[O:14][CH2:15][C:16]([OH:18])=[O:17])=[C:4](\[CH2:33][C:34]2[CH:39]=[CH:38][C:37]3[O:40][CH2:41][O:42][C:36]=3[CH:35]=2)/[C:3]([OH:43])=[O:2])=[CH:24][N:25]=1)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 1

HCID 22865619HCID 22865619, compound

Product 1

HCID 15388997HCID 15388997, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl-(E)-3(2-n-Butyl-1-methyl-1H-imidazol-5-yl)-3-(2-t-butoxycarbonylmethoxy-4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)prop-2-enoate (85 mg, 0.144 mmol) in 2.5N NaOH (1.0 ml) and isopropanol (2.0 ml) was heated under argon at 95° for 18 hours. The solvent (i-PrOH) was removed under reduced pressure and the residue was diluted with H2O and washed with EtOAc. The pH of the aqueous layer was lowered to 3.5 with 1M HCl and the solution was extracted with EtOAc (5x). The combined extracts were dried (Na2SO4 anhydrous) and evaporated. (48 mg, 64%). The crude title compound was recrystallized from CHCl3 /CH3CN to afford a white solid. (26 mg, 36%).

Workup

  1. customThe solvent (i-PrOH) was removed under reduced pressure
  2. additionthe residue was diluted with H2O
  3. washwashed with EtOAc
  4. extractionthe solution was extracted with EtOAc (5x)
  5. dry with materialThe combined extracts were dried (Na2SO4 anhydrous)
  6. customevaporated
  7. customThe crude title compound was recrystallized from CHCl3 /CH3CN
  8. customto afford a white solid

Sources & evidence

ORD record
ord-72529a83d5684194bf3bbb0de57ae5c9
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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