2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester → 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid

HRID 2381329노트

반응식

HRID 2381329 반응식
C[O:2][C:3](=[O:28])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](=[O:27])[CH3:26])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1>O1CCOCC1.Cl>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C:14]1[CH:13]=[N:12][N:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([OH:28])=[O:2])[C:16](=[O:17])[CH:15]=1)(=[O:27])[CH3:26]

참가 물질

4

반응물 1

HCID 668752142-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester

생성물 1

HCID 579192202-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid수율 53.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

반응 조건

온도
25 °C

실험 절차

A solution of 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (23.4 g, 0.061 mol) in 1,4-dioxane (230 mL) and hydrochloric acid (230 mL) was stirred at reflux overnight. After this time, the reaction was cooled to 25° C., concentrated in vacuo, and was treated with acetone (200 mL) and stirred at 25° C. for 1 h. The resulting precipitate was collected by filtration, washed with petroleum ether, acetone, ethyl acetate, and then dried to afford 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (12 g, 53%); ESI-MS 371 [M+H+]; HPLC: >98% (purity). 1H-NMR (300 MHz, DMSO-d6) δ 1.14 (m, 2H), 1.45 (m, 7H), 1.98 (m, 1H), 2.02 (m, 1H); 5.34 (m, 1H); 5.77 (s, 1H); 7.43 (m, 1H); 7.54 (m, 1H); 7.76 (m, 1H); 7.95 (m, 1H); 8.13 (m, 1H) 13.01 (s, 1H).

후처리

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. additionwas treated with acetone (200 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with petroleum ether, acetone, ethyl acetate
  6. customdried

출처 및 근거

ORD 기록
ord-8e0b311e549b48408a91f5bc1ec4d270
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258134B2

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