HCID 86749849, compound → HCID 70078934, compound

HRID 744000Notes

Reaction equation

HRID 744000 reaction equation
C[O:2][C:3](=[O:49])/[C:4](/[CH2:39][C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)=[C:5](/[C:21]1[N:25]([O:26][CH2:27][O:28][CH:29]([Si:31]([CH3:34])([CH3:33])[CH3:32])[CH3:30])[C:24]([CH2:35][CH2:36][CH2:37][CH3:38])=[N:23][CH:22]=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]CC)=[O:17]>[OH-].[Na+].C(O)(C)C>[CH2:35]([C:24]1[N:25]([O:26][CH2:27][O:28][CH:29]([Si:31]([CH3:32])([CH3:33])[CH3:34])[CH3:30])[C:21](/[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](\[CH2:39][C:40]2[CH:45]=[CH:44][C:43]3[O:46][CH2:47][O:48][C:42]=3[CH:41]=2)/[C:3]([OH:49])=[O:2])=[CH:22][N:23]=1)[CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 1

HCID 86749849HCID 86749849, compound

Product 1

HCID 70078934HCID 70078934, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl-(2E)-3(2-n-Butyl-1-trimethylsilylethyloxymethoxy-1H-imidazol-5-yl)-3-(2-ethoxycarbonylmethoxy-4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)prop-2-enoate (123 mg, 0.181 mmol) in 2.5N NaOH (2.0 ml) and isopropanol (2.0 ml) was heated under argon at 95° for 18 h. 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 3.5-4.5 with 1M HCl and the resultant precipitate was collected and air-dried (101 mg, 88%). The crude solid was recrystallized from i-propanol to afford the hydrochloride salt of the title compound as a white solid.

Workup

  1. customThe solvent (i-PrOH) was removed under reduced pressure
  2. additionthe residue was diluted with H2O
  3. washwashed with EtOAc
  4. customthe resultant precipitate was collected
  5. customair-dried (101 mg, 88%)
  6. customThe crude solid was recrystallized from i-propanol

Sources & evidence

ORD record
ord-e327706b686347deaeb7e054ee85c579
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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