tert.butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate → 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid

HRID 1154053Notes

Reaction equation

HRID 1154053 reaction equation
[C:1]([S:4][CH2:5][CH:6]1[CH2:21][N:9]2[CH2:10][CH2:11][CH2:12][CH:13]([C:14]([O:16]C(C)(C)C)=[O:15])[N:8]2[C:7]1=[O:22])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([S:4][CH2:5][CH:6]1[CH2:21][N:9]2[CH2:10][CH2:11][CH2:12][CH:13]([C:14]([OH:16])=[O:15])[N:8]2[C:7]1=[O:22])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 20435955tert.butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate

Product 1

HCID 204359472-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.69 of tert.butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate (diastereomer A) were treated with 10 ml of trifluoroacetic acid at room temperature for 2 hours. The solution was evaporated and the residue was re-evaporated with toluene several times. The residue was then crystallized from acetone to give 1.1 g of 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]-pyridazine-5-carboxylic acid having a melting point of 166°-168° C. (decomposition).

Workup

  1. customThe solution was evaporated
  2. customthe residue was re-evaporated with toluene several times
  3. customThe residue was then crystallized from acetone

Sources & evidence

ORD record
ord-6c7a35f1f7544e3bbc0905181ad06b9f
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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