Réaction #9704

Équation de réaction

sodium hydroxide

trans-methyl 2-({4′-[(5-fluoro-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentane-carboxylate

Methanol

→

title compound

Rendement 84.0%

trans-2-({4′-[(5-Fluoro-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)-cyclopentanecarboxylic acid

Rendement 84.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction was concentrated under reduced pressure
2. 2
   Autreto remove excess solvents
3. 3
   Autrethe residue was partitioned between water and chloroform/isopropanol (4:1)
4. 4
   workup.ADDITIONThe aqueous layer was adjusted to pH 2 by addition of aqueous phosphoric acid solution
5. 5
   AutreThe organic layer was then separated
6. 6
   Séchagedried (Na2SO4)
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Filtrationthe resulting solid was collected by filtration
9. 9
   Autredried in vacuo

Mode opératoire

A solution of 1 N aqueous sodium hydroxide solution (1 mL) was added to trans-methyl 2-({4′-[(5-fluoro-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentane-carboxylate (55 mg, 0.12 mmol) in THF (2 mL). Methanol was added until the mixture became homogeneous, and the resulting solution was heated at 60° C. for 1 h. The reaction was concentrated under reduced pressure to remove excess solvents, and the residue was partitioned between water and chloroform/isopropanol (4:1). The aqueous layer was adjusted to pH 2 by addition of aqueous phosphoric acid solution, with stirring. The organic layer was then separated, dried (Na2SO4), and concentrated under reduced pressure. The residue was suspended in acetone, and the resulting solid was collected by filtration and dried in vacuo to provide the title compound (45 mg, 84%). 1H NMR (300 MHz, acetone-d6) δ 10.40–10.10 (br s, 1 H), 8.15 (d, 2 H), 8.01 (d, 2 H), 7.87–7.82 (m, 5 H), 7.41 (dd, 1 H), 7.05–6.95 (m, 1 H), 4.26–4.17 (m, 1 H), 3.43–3.34 (m, 1 H), 2.31–2.23 (m, 1 H), 1.98–1.70 (m, 5 H); LC-MS m/z 461.3 (MH+), retention time 3.56 minutes.

Source