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Ethyl Acetate → 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid

HRID 2381400
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HRID 2381400 반응식
C[O:2][C:3](=[O:29])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[N:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][N:20]=3)[CH:13]=[N:12]2)[C:3]([OH:29])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 668752343-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester

생성물 1

HCID 579191163-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid methyl ester (0.2 g, 0.48 mmol) in dioxane (2 mL) was treated with a 6N aqueous sodium hydroxide solution (2 mL). The reaction was stirred at 25° C. for 2 d. At this point, ethyl acetate (20 mL) was added and then the aqueous phase was back extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Preparative HPLC afforded 3-cyclopentyl-2-[6-oxo-4-(4-trifluoromethyl-pyrimidin-2-yloxy)-6H-pyridazin-1-yl]-propionic acid as a light oil (20 mg, 10%); 1H NMR (300 MHz, DMSO-d6): δ 9.13 (d, 1H, J=4.8 Hz), 8.24 (d, 1H, J=2.4 Hz), 7.96 (d, 1H, J=4.8 Hz), 7.04 (d, 1H, J=2.4 Hz), 5.38 (dd, 1H, J1=4.5 Hz, J2=10.5 Hz), 2.25˜2.15 (m, 1H), 2.06˜1.97 (m, 1H), 1.71˜1.44 (m, 7H), 1.17˜1.04 (m, 3H). LC-MS: 399.1 [M+1]+, tR=3.04 min.

후처리

  1. extractionthe aqueous phase was back extracted with ethyl acetate
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-52e28379cbab45f1ac01062c95496535
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258134B2

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