Trifluoroacetic acid → HCID 10466657, compound

HRID 2218968Notes

Reaction equation

HRID 2218968 reaction equation
C(OC([NH:8][NH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[C:27]([O:33]C)(=O)[CH2:28][C:29]([CH3:31])=O>C(Cl)Cl>[C:16]([CH:13]1[CH2:12][CH2:11][CH:10]([N:9]2[C:27](=[O:33])[CH2:28][C:29]([CH3:31])=[N:8]2)[CH2:15][CH2:14]1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7757Methyl acetoacetateHCID 12319525HCID 12319525, compound

Product 1

HCID 10466657HCID 10466657, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To the N′-(4-tert-butyl-cyclohexyl)-hydrazinecarboxylic acid tert-butyl ester (7.61 g) in CH2Cl2 (30 mL) was added TFA (10 mL). After 5 h at RT, the solvent was removed under reduced pressure. The residue was dissolved in glacial acetic acid (100 mL), methyl acetoacetate (4.46 g, 38.4 mmol) was added and the reaction was heated to 100° C. for 18 h. After allowing the reaction to cool to RT, the solvent was removed under reduced pressure. Flash chromatography of the residue (50% to 80% EtOAc/hexanes, silica gel) gave the two isomers of 2-(4-tert-butyl-cyclohexyl)-5-methyl-2,4-dihydro-pyrazol-3-one as pale yellow oils. Isomer 1: 2.67 g; TLC Rf 0.30 (silica gel, 1:1 EtOAc/hexanes); MS (ES+) m/z 237.0 (M+H+). Isomer 2: 0.66 g; TLC Rf 0.15 (silica gel, 1:1 EtOAc/hexanes); MS (ES+) m/z 237.4 (M+H+).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in glacial acetic acid (100 mL)
  3. customthe reaction
  4. temperatureto cool to RT
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6440d0b29054461884d003c5ece50e94
Source dataset
uspto-grants-2008_08
Patent number
US07414040B2

Reaction notes

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