Sodium Hydroxide → HCID 22660176, compound

HRID 393417Notes

Reaction equation

HRID 393417 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3([C:18]([O:20]C)=[O:19])[CH2:17][CH2:16][CH2:15]3)=[CH:9][CH:8]=2)=[N:5][N:4]=[N:3]1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]3([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:12]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22660212HCID 22660212, compound

Product 1

HCID 22660176HCID 22660176, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of methyl 1-[[4-(1-methyltetrazol-5-yl)phenyl]methyl]cyclobutane carboxylate (0.33 g, 1.15 mmol) in a mixture of THF (7 mL) and methanol (7 mL) was added 1 N sodium hydroxide (7 mL). The mixture was heated to 55° C. and stirred for 4 h at which point TLC analysis indicated the absence of starting material. After cooling to room temperature, the solvent was removed under vacuum and the residue was diluted with water and extracted with ethyl acetate to remove any neutral impurities. Then, the aqueous layer was neutralized with 1 N hydrochloric acid and the product was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with saturated brine and dried over sodium sulfate. After filtration, the solution was concentrated under vacuum and the residue was dried under high vacuum to afford 1-[[4-(1-methyl-5-tetrazolyl)phenyl]methyl]cyclobutane carboxylic acid (180 mg, 57%) as a light yellow syrup.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under vacuum
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. customto remove any neutral impurities
  6. extractionthe product was extracted with ethyl acetate (2×50 mL)
  7. washThe combined extracts were washed with saturated brine
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe solution was concentrated under vacuum
  11. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-a9fb8398fe9c4e03b4912fa5d71e82f4
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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