Ethanol → HCID 86587208, compound

HRID 397847Notes

Reaction equation

HRID 397847 reaction equation
[C:1]([CH2:4][C:5]1[NH:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([OH:3])=[O:2].CO.[CH3:13][CH2:14][OH:15].[CH3:16][CH:17](C)C(Cl)=O>O1CCOCC1.C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:1]([CH2:4][C:5]1[NH:9][N:8]=[C:7]([NH:10][C:14]([CH2:13][CH2:16][CH3:17])=[O:15])[CH:6]=1)([OH:3])=[O:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 62325Isobutyryl chlorideHCID 16221512(5-Amino-2H-pyrazol-3-yl)-acetic acid

Product 1

HCID 86587208HCID 86587208, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution consisting of 398 mg of 5-carboxymethyl-3-aminopyrazole (synthesized as described above for the 5-ethyl analog, by use of MeOH rather than EtOH in the esterification) and 440 mL of pyridine in 5 ml of anhydrous dioxane was cooled to 0° C. To this solution was slowly added 621 mL of 2-methylpropanoyl chloride. The reaction was allowed to stir at room temperature for two hours, diluted with 25 ml of chloroform and extracted once against 15 ml of 1 M HCl followed by 15 ml of saturated NaHCO3. The organic layer was isolated and dried over MgSO4 and the solvent was removed under vacuum. The product was used in the next step without further purification.

Workup

  1. customsynthesized
  2. extractionextracted once against 15 ml of 1 M HCl
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed under vacuum
  6. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-da323b9eef1a4cdc959845fdb22f6eeb
Source dataset
uspto-grants-2003_08
Patent number
US06610724B2

Reaction notes

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