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

HRID 30925ノート

反応式

HRID 30925 の反応式
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([C@@H:27]5[CH2:31][CH2:30][CH2:29][C@H:28]5[C:32]([O:34]C)=[O:33])=[O:26])=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)=[N:9][C:8]=2[CH:36]=1.CO>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([C@@H:27]5[CH2:31][CH2:30][CH2:29][C@H:28]5[C:32]([OH:34])=[O:33])=[O:26])=[CH:21][CH:20]=4)=[CH:17][CH:18]=3)=[N:9][C:8]=2[CH:36]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11984509trans-Methyl 2-({4'-[(5-fluoro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentane-carboxylate

生成物 1

HCID 11984466trans-2-({4'-[(5-Fluoro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-yl}carbonyl)cyclopentanecarboxylic acid収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

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.

後処理

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove excess solvents
  3. customthe residue was partitioned between water and chloroform/isopropanol (4:1)
  4. additionThe aqueous layer was adjusted to pH 2 by addition of aqueous phosphoric acid solution
  5. customThe organic layer was then separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-48fda4e982c94b80981203e306d3a297
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

反応ノート

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