Lithium Hydroxide → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid

HRID 1515654노트

반응식

HRID 1515654 반응식
C([O:3][C:4](=[O:35])[C:5]([O:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[CH2:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[NH:15][C:12]2=[N:13][CH:14]=1)([CH3:7])[CH3:6])C.[OH-].[Li+]>O1CCCC1.O>[CH:20]1([CH:19]=[C:18]([C:16]2[NH:15][C:12]3=[N:13][CH:14]=[C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:35])=[O:3])[CH:10]=[C:11]3[CH:17]=2)[C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 583052662-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid ethyl ester

생성물 1

HCID 672290332-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid수율 92.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid ethyl ester (prepared as in Example 26, 120 mg, 0.24 mmol) in tetrahydrofuran (10 mL) and water (2.5 mL) was added lithium hydroxide (48 mg, 2 mmol) at room temperature and the mixture was stirred for 12 h. The resulting mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-2-methyl-propionic acid (60 mg, 92.3%) as a white solid: LC/MS m/e calcd for C25H30N2O5S [M+H]+ 471.59, observed 471.6; 1H NMR (400 MHz, CD3OD) δ ppm 1.24 (m, 2H), 1.51 (m, 2H), 1.57 (s, 6H), 1.60-1.88 (m, 5 H, H), 2.13 (m, 1H), 2.27 (m, 1H), 3.08 (s, 3H), 4.32 (t, J=7.8 Hz, 1H), 6.50 (s, 1H), 7.59 (d, J=8.3 Hz, 2H), 7.85 (d, J=2.3 Hz, 1H), 7.89 (d, J=8.3 Hz, 2H), 7.97 (br. d., 1H).

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-028bb8a45d774819a51b6a0a88591e88
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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