Reacción #1929082

ord-0b226b9005804d24a12c0a54af2801a8

Ecuación de reacción

Cl
hydrochloric acid
COC(=O)C1(NC(=O)Cc2cc(-c3ccc(Cl)cc3)ccc2Cl)CCC(F)(F)CC1
compound
COC(=O)C1(NC(=O)Cc2cc(-c3ccc(Cl)cc3)ccc2Cl)CCC(F)(F)CC1
Methyl 1-{[(4,4′-dichlorobiphenyl-3-yl)acetyl]amino}-4,4-difluorocyclohexanecarboxylate
CC(=O)N(C)C
DMA
CC(=O)N(C)C
DMA
CC(C)(C)[O-].[K+]
potassium tert-butoxide
O=C1NC2(CCC(F)(F)CC2)C(O)=C1c1cc(-c2ccc(Cl)cc2)ccc1Cl
title compound
O=C1NC2(CCC(F)(F)CC2)C(O)=C1c1cc(-c2ccc(Cl)cc2)ccc1Cl
3-(4,4′-Dichlorobiphenyl-3-yl)-8,8-difluoro-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

3.20 g (5.74 mmol) of the compound from Example 8A were initially charged in a solution of 14 ml of DMA (N,N-dimethylacetamide), a solution of 9 ml of DMA and 1.69 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 1.50 g (52% of theory) of the title compound of melting point m.p. 156° C.

Fuente

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