Nitrogen → 2-(3-Acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid

HRID 1189391Notes

Reaction equation

HRID 1189391 reaction equation
N#N.C([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[N:15]2)[O:11][CH:12]=1)=[O:7])C.[OH-].[Na+]>C1COCC1.Cl>[C:19]([C:16]1[CH:17]=[CH:18][N:14]([CH2:13][C:10]2[O:11][CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=2)[N:15]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 671284172-(3-Acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

Product 1

HCID 671287672-(3-Acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(3-acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester (137 mg, 0.52 mmol) in THF (5.0 mL) was treated at rt with 1N NaOH (2.5 mL, 2.5 mmol) and the reaction mixture was stirred for 3 h at rt. The reaction mixture was poured in 1N HCl (23 mL) and extracted with EA (50 mL). The org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give the crude 2-(3-acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid as a deep brown foam. LC-MS-conditions 02: tR=0.64 min, [M+H]+=236.13.

Workup

  1. extractionextracted with EA (50 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c845448f96bc494880a3c51bdb5455ab
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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