Reacción #2358580

ord-23292a138d554335ad750e47d2e6f613

Ecuación de reacción

COC(=O)c1cc([C@H](O)CO)cc(-c2ccc(Oc3ccc(F)cc3)cc2)n1
(S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate
C1CCOC1
THF
O.[Li][OH]
LiOH.H2O
O=C(O)c1cc([C@H](O)CO)cc(-c2ccc(Oc3ccc(F)cc3)cc2)n1
(S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinic acid

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothen evaporated in vacuo
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in 5 mL water
  3. 3
    Filtraciónfiltered
  4. 4
    OtroThe mixture was evaporated in vacuo

Procedimiento

To the crude (S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate (assume 0.884 mmol) in 5 mL of a 5:1 mixture of THF and water was added LiOH.H2O (0.084 g, 2.00 mmol). The reaction was stirred overnight then evaporated in vacuo. The residue was dissolved in 5 mL water, filtered and acidified with 2.00 mL 1N HCl. The mixture was evaporated in vacuo to give the product (S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinic acid mixed with lithium chloride (LC/MS: m/z=370.2 [M+H]+).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09120752B2uspto-grants-2015_09