Hydrochloric Acid → HCID 178441662, compound

HRID 2372846Notes

Reaction equation

HRID 2372846 reaction equation
[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:9](=[O:29])[C:8]([C:30]([O:32]CC)=[O:31])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CO.Cl>O>[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:9](=[O:29])[C:8]([C:30]([OH:32])=[O:31])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 178441661HCID 178441661, compound

Product 1

HCID 178441662HCID 178441662, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared by treating 2-n-butyl-3-(2'-(tetrazol-5-yl)-biphen-4-yl)methyl-5-ethoxycarbonylpyrimidin-4(3H)-one (from Example 8) with an ester hydrolyzing agent such as sodium hydroxide in an appropriate solvent such as methanol, possibly with heating. Addition of water, acidification with concentrated HCl, saturation with NaCl, extraction with ether, washing of the combined organic extracts with brine, drying of the organic material over an appropriate drying agent such as MgSO4, and stripping of solvent in vacuo should give the crude organic acid which may then be purified by appropriate means such as silica gel chromatography. Alternatively, the ester from Example 8 is hydrolyzed using an appropriate esterase such as pig liver esterase followed by standard purification procedures.

Workup

  1. temperaturepossibly with heating
  2. extractionwith NaCl, extraction with ether
  3. washwashing of the combined organic extracts with brine
  4. dry with materialdrying of the organic material over an appropriate drying agent such as MgSO4, and stripping of solvent in vacuo
  5. customshould give the crude organic acid which
  6. custommay then be purified by appropriate means such as silica gel chromatography
  7. customfollowed by standard purification procedures

Sources & evidence

ORD record
ord-800475e20a934ec5ac1d91c1394926ce
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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