Pyridine → HCID 22865617, compound

HRID 744001Notes

Reaction equation

HRID 744001 reaction equation
[CH2:1]([C:5]1[N:6](OCOC([Si](C)(C)C)C)[C:7](/[C:10](/[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[O:33][CH2:34][C:35]([OH:37])=[O:36])=[C:11](\[CH2:15][C:16]2[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)/[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[OH-].[Na+]>O.Cl.[Cl-].[Na+].O>[CH2:1]([C:5]1[NH:6][C:7](/[C:10](/[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[O:33][CH2:34][C:35]([OH:37])=[O:36])=[C:11](\[CH2:15][C:16]2[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)/[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 70078934HCID 70078934, compound

Product 1

HCID 22865617HCID 22865617, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a flask containing (2E)-3(2-n-butyl-1-trimethylsilylethyloxymethoxy-1H-imidazol-5-yl)-3-(2-carboxymethoxy-4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)prop-2-enoic acid (32 mg, 0.05 mmol) was added at 0° HF.pyridine (3 ml) and the reaction stirred for 15 min. The solution was diluted with water (1-2 ml), 3N HCl (1 ml), and brine (2 ml). The pH was raised to 3.5 with addition of 2.5N NaOH and the solution extracted with EtOAc (5x). The EtOAc was removed under reduced pressure and the residue taken up in water which was acidified to pH 3.5 with 1 drop of 1N HCl. The copious white ppt was collected and air dried to afford the hydrochloride salt of the title compound as a tan solid. (15 mg, 59% )

Workup

  1. additionwas added at 0° HF
  2. extractionthe solution extracted with EtOAc (5x)
  3. customThe EtOAc was removed under reduced pressure
  4. customThe copious white ppt was collected
  5. customair dried

Sources & evidence

ORD record
ord-06334424b8324035b3fe3f449135f993
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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