Sodium Hydroxide → 2-Dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetic acid

HRID 1756919Notes

Reaction equation

HRID 1756919 reaction equation
[OH-].[Na+].[CH2:3]([N:15]1[N:19]=[N:18][C:17]([C:20]([F:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]CC)=[O:22])=[N:16]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CO.O>[CH2:3]([N:15]1[N:19]=[N:18][C:17]([C:20]([F:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([OH:23])=[O:22])=[N:16]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 586632482-Dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetic acid, ethyl ester

Product 1

HCID 539372962-Dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

NaOH (0.12 g, 3 mole) was added in one portion to a stirred solution of 2-dodecyl-α-fluoro-α-phenyl-2H-tetrazole-5-acetic acid, ethyl ester (0.59 g, 1.4 mole) dissolved in 6 mL of 5:1 CH3OH-H2O at room temperature. After stirring for 3 hours, the mixture was concentrated, diluted with H2O, acidified with 6N HCl (pH 1) and extracted with ethyl acetate (2×150 mL). The combined ethyl acetate extracts were washed with brine (50 mL) and dried. Filtration and concentration afforded 0.5 g (91%) of the title compound as an oil.

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. washThe combined ethyl acetate extracts were washed with brine (50 mL)
  5. customdried
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-bac896e75b3549d48d5b2b2d934f0b4a
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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