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

HRID 9608노트

반응식

HRID 9608 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-89e1b566444047c999b485ad57944331
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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