Water → 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

HRID 1189534노트

반응식

HRID 1189534 반응식
[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([O:27]CC)=[O:26])[C:4]=1[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:2].O.O.[OH-].[Li+]>O1CCCC1>[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([OH:27])=[O:26])[C:4]=1[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2회HCID 53247599ethyl 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

생성물 1

HCID 532476002-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (485 mg, 0.975 mmol) in tetrahydrofuran (2.9 mL), and water (0.98 mL), was added solid lithium hydroxide monohydrate (40.9 mg, 0.975 mmol). The reaction was stirred at room temperature for 45 minutes, after which analysis by LCMS indicated that the reaction was not complete. After 20 more minutes, an additional equivalent of lithium hydroxide monohydrate (40.9 mg) was added, and the reaction was stirred at room temperature for an additional 20 minutes, after which it was determined to be complete by LCMS analysis. Concentration of the reaction mixture, followed by acidification with aqueous 3M hydrochloric acid solution (0.65 mL), extraction with dichloromethane (1×50 mL), then ethyl acetate (2×50 mL), drying (sodium sulfate), filtering and concentration afforded 2-(3-cyano-2-cyclohexyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (442 mg, 0.941 mmol, 97% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.96 (d, 1H), 7.43 (app. t, 1H), 7.32 (dd, 1H), 7.04 (d, 1H), 4.57 (s, 2H), 4.29 (s, 2H), 3.33-3.36 (m, 4H), 2.50 (m, 1H), 1.93-1.96 (m, 7H), 1.70-1.88 (m, 8H), 1.28-1.32 (m, 2H).

후처리

  1. stirringthe reaction was stirred at room temperature for an additional 20 minutes
  2. extractionConcentration of the reaction mixture, followed by acidification with aqueous 3M hydrochloric acid solution (0.65 mL), extraction with dichloromethane (1×50 mL)
  3. dry with materialethyl acetate (2×50 mL), drying (sodium sulfate)
  4. filtrationfiltering
  5. concentrationconcentration

출처 및 근거

ORD 기록
ord-862ffa70b9db42728cb00087026e7064
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674115B2

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