Hydrochloric Acid → (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid

HRID 18950

반응식

HRID 18950 반응식
C[O:2][C:3](=[O:19])[C@@H:4]([N:11]1[CH2:15][C:14]([O:16][CH3:17])=[CH:13][C:12]1=[O:18])[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:11]2[CH2:15][C:14]([O:16][CH3:17])=[CH:13][C:12]2=[O:18])[C:3]([OH:19])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66895025(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester

생성물 1

HCID 66894643(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid수율 65%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution containing (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (1.42 g, 5.20 mmol) in tetrahydrofuran (10 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (273 mg, 6.4 mmol) in water (10 mL). The mixture was stirred at 25° C. for 2.5 h, it was then acidified with 2N aqueous hydrochloric acid. The mixture was extracted with dichloromethane (2×30 mL). The combined organic layers was dried over magnesium sulfate and concentrated to afford (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid, (855 mg, 65%), as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (m, 2H), 1.36-1.88 (m, 9H), 3.78 (s, 3H), 3.95 (J=17.7 Hz, 2H), 4.54 (dd, J=4.5 Hz, 11.0 Hz, 1H), 5.16 (s 1H), 12.80 (s, 1H).

후처리

  1. extractionThe mixture was extracted with dichloromethane (2×30 mL)
  2. dry with materialThe combined organic layers was dried over magnesium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-20c64ddd147f4b89aa4a9d5b75f1c697
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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