Lithium Hydroxide → 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid
반응식
[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:26][C:27]([O:29]CC)=[O:28])[C:6]([CH3:25])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]=1[CH3:9].[Li+].[OH-]>C1COCC1.CO.O>[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:26][C:27]([OH:29])=[O:28])[C:6]([CH3:25])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)(=[O:18])=[O:19])=[CH:13][CH:12]=2)[C:8]=1[CH3:9]참가 물질
6
반응물 2
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 25 °C
실험 절차
Ethyl 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (20 mg, 0.045 mmol) in THF (2.0 ml), MeOH (0.500 ml) and water (0.50 ml) was stirred and LiOH (4.27 mg, 0.178 mmol) was added. The resulting mixture was stirred at 25° C. for two hours. The solvent was then removed and water was added, followed by 1 N HCl. The solvent was again removed, MeOH was added, and the resulting solution purified by preparative HPLC to give 12 mg of a light blue solid (12 mg, 0.029 mmol, 64.0% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.63 (d, 2H), 7.19 (d, 2H), 4.57 (s, 2H), 3.76 (s, 2H), 3.66 (t, 2H), 3.18-3.15 (m, 4H), 2.76-2.73 (m, 4H), 2.03 (s, 3H), 1.78 (s, 3H), 1.70-1.66 (m, 4H).
후처리
- customThe solvent was then removed
- additionwater was added
- customThe solvent was again removed
- additionMeOH was added
- customthe resulting solution purified by preparative HPLC
출처 및 근거
- ORD 기록
- ord-78aa3118824d4cd684cbb70d3c1a26c9
- 출처 데이터셋
- uspto-grants-2014_03
- 특허 번호
- US08674115B2
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