反応 #59203

反応方程式

sodium hydroxide

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

Methanol

→

title compound

収率 84.0%

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

収率 84.0%

溶媒

THF

反応条件

後処理

1. 1
   濃縮The reaction was concentrated under reduced pressure
2. 2
   その他to remove excess solvents
3. 3
   その他the 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
   その他The organic layer was then separated
6. 6
   乾燥dried (Na2SO4)
7. 7
   濃縮concentrated under reduced pressure
8. 8
   ろ過the resulting solid was collected by filtration
9. 9
   その他dried in vacuo

実験手順

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)cyclopentanecarboxylate (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, 1H), 8.15 (d, 2H), 8.01 (d, 2H), 7.87-7.82 (m, 5H), 7.41 (dd, 1H), 7.05-6.95 (m, 1H), 4.26-4.17 (m, 1H), 3.43-3.34 (m, 1H), 2.31-2.23 (m, 1H), 1.98-1.70 (m, 5H); LC-MS m/z 461.3 (MH+), retention time 3.56 minutes.

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