Ammonia → (+/-)-3-(2-Pyridyl)-4,5-dihydro-1-(3-mercapto-1-oxopropyl)-1H-pyrazole-5-carboxylic acid

HRID 127001Notes

Reaction equation

HRID 127001 reaction equation
N.C([S:5][CH2:6][CH2:7][C:8]([N:10]1[CH:14]([C:15]([OH:17])=[O:16])[CH2:13][C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:11]1)=[O:9])(=O)C>>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:12]1[CH2:13][CH:14]([C:15]([OH:17])=[O:16])[N:10]([C:8](=[O:9])[CH2:7][CH2:6][SH:5])[N:11]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 20288727(+/-)-1-[3-(Acetylthio)-1-oxopropyl]-3-(2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Product 1

HCID 20288735(+/-)-3-(2-Pyridyl)-4,5-dihydro-1-(3-mercapto-1-oxopropyl)-1H-pyrazole-5-carboxylic acid

Procedure

Aqueous ammonia (12 ml of 7 N) is stirred at 0°-5° C. under argon and 3.5 g of (±)-1-[3-(acetylthio)-1-oxopropyl]-3-(2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid is added. The resulting solution is stirred for 2 hours under argon and is then extracted with ethyl acetate (discarded). The aqueous layer is acidified with acetic acid and extracted with ethyl acetate (three 50 ml portions). The combined organic layers are washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound.

Workup

  1. extractionis then extracted with ethyl acetate (discarded)
  2. extractionextracted with ethyl acetate (three 50 ml portions)
  3. washThe combined organic layers are washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71cc72670eb44bdeabe440da9b22a19b
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Reaction notes

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