Lithium Hydroxide → 1-[2-(Dimethylamino)-2-oxoethyl]-3-(1,1-dimethylethyl)-1H-pyrazole-5-carboxylic acid

HRID 1930423Notes

Reaction equation

HRID 1930423 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12]CC)=[O:11])[N:7]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66729263HCID 66729263, compound

Product 1

HCID 690374861-[2-(Dimethylamino)-2-oxoethyl]-3-(1,1-dimethylethyl)-1H-pyrazole-5-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-tert-butyl-1-(2-(dimethylamino)-2-oxoethyl)-1H-pyrazole-5-carboxylate from example B17 (0.48 g, 1.7 mmol) in THF (10 mL) was added a solution of lithium hydroxide (0.21 g, 5.1 mmol) in water (5 mL) and the mixture was stirred for 16 h at RT. Solvents were removed and the residue was acidified with 3M HCl and the product was extracted with EtOAc (2×30 ml). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to afford 3-tert-butyl-1-(2-(dimethylamino)-2-oxoethyl)-1H-pyrazole-5-carboxylic acid (0.4, 93% yield) as a pasty mass. 1H NMR (400 MHz, DMSO-d6): δ 6.69 (s, 1H), 5.30 (s, 2H), 3.02 (s, 3H), 2.82 (s, 3H), 1.24 (m, 9H); MS (ESI) m/z: 254.0 (M+H+).

Workup

  1. customSolvents were removed
  2. extractionthe product was extracted with EtOAc (2×30 ml)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d5576ea9cff45899d193791bcca04a7
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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