Reacción #2254180

ord-d632c73ed8c04d9480f4f695ecf513c4

Ecuación de reacción

CC(=O)[O-].[Na+]
Sodium acetate
Cl.NO
hydroxylamine hydrochloride
Cc1cc(C=O)sc1C(=O)NCC(F)(F)F
5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide
Cc1cc(C=NO)sc1C(=O)NCC(F)(F)F
5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe reaction is quenched with water
  2. 2
    ExtracciónThe reaction mixture is extracted three times with ethyl acetate
  3. 3
    SecadoThe combined organic phases are dried over Na2SO4
  4. 4
    Concentraciónconcentrated in vacuo

Procedimiento

Sodium acetate (90 mg) is added to a solution of hydroxylamine hydrochloride (60 mg) and 5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (190 mg) in THF (5 ml), water (1 ml) and DMSO (1 ml). After 3 hours at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated in vacuo to yield 5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide. The crude product obtained (206 mg, yellowish oil) is used without further purification. MS (HPLC/MS): 267 (MH+). Retention time: 2.56 min and 2.64 min (two diastereoisomers).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09044389B2uspto-grants-2015_06