Methanol → HCID 19977036, compound

HRID 1450520Notes

Reaction equation

HRID 1450520 reaction equation
[OH-:1].[Na+].[CH3:3][N:4]([CH3:28])[C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[N:14][N:15]([CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)[N:16]=2)[CH:8]=[CH:9][C:10]=1O.[CH3:29][OH:30]>>[CH3:3][N:4]([CH3:28])[C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[N:14][N:15]([CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:1][C:29](=[O:30])[C:7]([CH3:12])([CH3:8])[CH3:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 135812614HCID 135812614, compound

Product 1

HCID 19977036HCID 19977036, compoundYield 12%

Conditions

Temperature
50 °C

Procedure

To a solution of aqueous 10% sodium hydroxide (0.67 ml) in methanol (5 ml) was added methyl 4-[5-(3-dimethylamino-4-hydroxyphenyl)tetrazol-2-ylmethyl]benzoate (296 mg) obtained in reference example 6. The mixture was heated at 50° C. for 1 h, and the solvent was evaporated. To the residue were added acetone (10 ml) and H2O (10 ml), and pivaloyl chloride (150 mg) was added dropwise to it under ice cooling. The mixture was stirred at the same temperature for 1 h, acidified with aqueous citric acid, and extracted with ethyl acetate. The extract was dried and evaporated to dryness. The residue was purified by column chromatography on silica gel with chloroform-methanol (100/4-5) as an eluate to give 46 mg (12%) of the title compound.

Workup

  1. customobtained in reference example 6
  2. customthe solvent was evaporated
  3. additionTo the residue were added acetone (10 ml) and H2O (10 ml), and pivaloyl chloride (150 mg)
  4. additionwas added dropwise to it under ice cooling
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography on silica gel with chloroform-methanol (100/4-5) as an eluate

Sources & evidence

ORD record
ord-b7a96822e39e4ed3b0fced453a686aa7
Source dataset
uspto-grants-1997_02
Patent number
US05602161

Reaction notes

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