Sodium Hydroxide → HCID 71259112, compound

HRID 1630321Notes

Reaction equation

HRID 1630321 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]2[N:16]([N:26]=[C:27]([C:29]([O:31]CC)=[O:30])[CH:28]=2)[C:17]=1[C:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]2[N:16]([N:26]=[C:27]([C:29]([OH:31])=[O:30])[CH:28]=2)[C:17]=1[C:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71267854HCID 71267854, compound

Product 1

HCID 71259112HCID 71259112, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylcyclohex-1-en-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (185 mg, 0.392 mmol) in EtOH (4 mL) was added 1N NaOH (0.392 mL, 0.392 mmol) and the resulting mixture was stirred at room temp for 4 h. A this point LCMS indicated completion of reaction. Solvents were then removed under reduced pressure and the mixture was diluted with water (3 mL), acidified with 1N HCl, extracted with ethyl acetate (25 mL), washed with brine (10 mL), dried (Na2SO4), filtered and concentrated to afford (S)-6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4,4-dimethylcyclohex-1-en-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylic acid (150 mg, 0.338 mmol, 86% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.15 (s, 1H), 6.26 (br. s., 0.6H), 5.93 (br. s., 0.4H), 5.53 (s, 0.6H), 5.46 (s, 0.4H), 4.29-4.19 (m, 2H), 2.79 (s, 1H), 2.72 (s, 2H), 2.19-2.14 (m, 2H), 1.77-1.54 (m, 4H), 1.29-1.16 (m, 18H). LCMS (M+H)=444.4.

Workup

  1. customcompletion of reaction
  2. customSolvents were then removed under reduced pressure
  3. additionthe mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (25 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cdb05c1a674d473b96c0ec7adc39647b
Source dataset
uspto-grants-2014_07
Patent number
US08791108B2

Reaction notes

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