Ethyl Acetate → 1-{[(3-Phenylpropanoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

HRID 492055노트

반응식

HRID 492055 반응식
[C:1]1(/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH2:13][O:14][C:15]([NH:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19]2)=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)C>[Pd].C(O)C>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]([NH:17][C:18]2([C:21]([OH:23])=[O:22])[CH2:19][CH2:20]2)=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 247984111-{[((2E)-3-Phenylprop-2-enoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

생성물 1

HCID 247984941-{[(3-Phenylpropanoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid수율 80.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A dry 100 mL round-bottomed flask equipped with a magnetic stir bar and a rubber septum was charged with 1-{[((2E)-3-phenylprop-2-enoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic acid (16) (0.8 g, 2.5 mmols) and 10% palladium on carbon in 1:1 mixture of ethylacetate and ethanol. The reaction was done at 1 atm pressure under a hydrogen balloon at room temperature. After the reaction was complete, the solution was filtered through Celite and the solvents removed in vacuo using a rotary evaporator. The dry, crude residue was dissolved in a small amount of a mixture of 60% (v/v) acetonitrile/water (ca. 10 mL), and the solution filtered through a 0.2 μm nylon syringe filter. Final purification was achieved by mass-guided preparative HPLC. After lyophilization of the solvents, 0.646 g (80% yield) of the title compound (17) was obtained as a white solid. M.p: 132.9-134.4° C. 1H NMR (CDCl3, 400 MHz): δ=7.31 (t, 2H), 7.19 (t, 3H), 6.82 (q, 1H), 6.38 (s, 0.3H), 5.50 (s, 0.7H), 2.99 (t, 2H), 2.72 (m, 2H), 1.71 (m, 2H), 1.42 (d, 3H), 1.30 (m, 2H). MS (ESI) m/z 343.93 (M+Na)+, 319.96 (M−H)−.

후처리

  1. customA dry 100 mL round-bottomed flask equipped with a magnetic stir bar
  2. customat room temperature
  3. filtrationthe solution was filtered through Celite
  4. customthe solvents removed in vacuo
  5. customa rotary evaporator
  6. dissolutionThe dry, crude residue was dissolved in a small amount of a mixture of 60% (v/v) acetonitrile/water (ca. 10 mL)
  7. filtrationthe solution filtered through a 0.2 μm nylon syringe
  8. filtrationfilter
  9. customFinal purification

출처 및 근거

ORD 기록
ord-7ff0656ebe8148339b6ebff22a735c9b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531572B2

반응 노트

불러오는 중…