Ethyl levulinate → 1H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-

HRID 344741

반응식

HRID 344741 반응식
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].O=[C:10]([CH3:18])[CH2:11][CH2:12][C:13](OCC)=[O:14]>O>[O:5]=[C:4]1[CH2:3][N:2]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2([CH3:18])[NH:6]1

참가 물질

5

반응물 3

HCID 10883Ethyl levulinateHCID 14798Sodium HydroxideHCID 2723639Glycinamide hydrochloride

생성물 1

HCID 30795901H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-수율 21%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of glycinamide hydrochloride (18.4 g, 0.166 mol) in water (200 ml), adjusted to pH 9.5 with 10% sodium hydroxide (about 60 ml), ethyl 4-oxopentanoate (20 g, 0.139 mol) was added. The solution was refluxed for 24 hours. After cooling the solvent was evaporated under vacuum and the residue was chromatographed over silica gel (dichloromethane-methanol 9:1) to afford 4.5 g (21%) of the title compound, m.p. 187°-189° C. NMR (CDCl3): deltaH =4.17 and 3.53 (ABq, J=16 Hz, 2H, NCH2CO), 1.5 (s, 3H, CH3). MS (E.I., 70 eV, 1.5 mA) m/z=154 (M+), 139 (M--CH3)+, 111 (M--CONH)+.

후처리

  1. additionwas added
  2. temperatureThe solution was refluxed for 24 hours
  3. temperatureAfter cooling the solvent
  4. customwas evaporated under vacuum
  5. customthe residue was chromatographed over silica gel (dichloromethane-methanol 9:1)

출처 및 근거

ORD 기록
ord-6ad2ce07f5384ac7a74581258ecdfb37
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053422

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