Water → HCID 178425325, compound

HRID 243710Notes

Reaction equation

HRID 243710 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]([CH3:13])[C:8]([O:10]CC)=[O:9])[NH:4][N:3]=1.O.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]([CH3:13])[C:8]([OH:10])=[O:9])[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178470994HCID 178470994, compound

Product 1

HCID 178425325HCID 178425325, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.24 g (6.8 mmol) of ethyl 2-(3-methyl-1H-pyrazol-5-yl)propanoate from step B above in 20 mL of methanol and 5 mL of water was added 1.5 mL (7.5 mmol) of an aqueous 5.0 M sodium hydroxide solution. The resulting mixture was stirred at ambient temperature for 2.5 h and then evaporated in vacuo to remove the methanol. The aqueous phase was extracted with ethyl acetate (2×75 mL) then acidified with a 2 N hydrochloric acid solution until a pH of 4 was achieved. The aqueous solution was extracted with ethyl acetate (5×50 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound as a yellow gum (0.80 g, 76%). 1H NMR (CDCl3, 500 MHz) δ 10.23 (br s, 1H), 7.26 (s, 1H), 5.97 (s, 1H), 3.87 (q, J=7.3 Hz, 1H), 2.26 (s, 3H), 1.59 (d, J=7.3 Hz, 3H). LC-MS: m/z (ES) 155 (MH)+.

Workup

  1. customevaporated in vacuo
  2. customto remove the methanol
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×75 mL)
  4. extractionThe aqueous solution was extracted with ethyl acetate (5×50 mL)
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dd90c78ddd484fa79565d80461268a4f
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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