Reacción #1929081

ord-f0c18b8a86a34e51ad1a36a4a3bf9cda

Ecuación de reacción

Cl
hydrochloric acid
COC(=O)C1(NC(=O)Cc2cc(-c3ccc(F)cc3)ccc2C)CCC(F)(F)CC1
compound
COC(=O)C1(NC(=O)Cc2cc(-c3ccc(F)cc3)ccc2C)CCC(F)(F)CC1
Methyl 4,4-difluoro-1-{[(4′-fluoro-4-methylbiphenyl-3-yl)acetyl]amino}cyclohexanecarboxylate
CC(=O)N(C)C
DMA
CC(=O)N(C)C
DMA
CC(C)(C)[O-].[K+]
potassium tert-butoxide
Cc1ccc(-c2ccc(F)cc2)cc1C1=C(O)C2(CCC(F)(F)CC2)NC1=O
title compound
Cc1ccc(-c2ccc(F)cc2)cc1C1=C(O)C2(CCC(F)(F)CC2)NC1=O
8,8-Difluoro-3-(4′-fluoro-4-methylbiphenyl-3-yl)-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe resulting residue was filtered off with suction
  2. 2
    OtroPurification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1)

Procedimiento

2.80 g (5.94 mmol) of the compound from Example 7A were initially charged in a solution of 8 ml of DMA (N,N-dimethylacetamide), a solution of 5 ml of DMA and 1.75 g (2.5 eq.) of potassium tert-butoxide was added dropwise at 20° C. and the mixture was stirred at room temperature for 4 h. The mixture was poured into 200 ml of water and the reaction was adjusted to pH 2 using concentrated aqueous hydrochloric acid, and the resulting residue was filtered off with suction. Purification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1) gave 1.07 g (44% of theory) of the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08946124B2uspto-grants-2015_02