Propionic Acid → N-[2-(1,2,3,7,8,9-hexahydro-2-oxoindeno[5,4-b][1,4]oxazin-9-yl)ethyl]propionamide

HRID 1636623노트

반응식

HRID 1636623 반응식
Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:24]([OH:28])(=O)[CH2:25][CH3:26].[NH2:29][CH2:30][CH2:31][CH:32]1[C:44]2[C:43]3[NH:42][C:41](=[O:45])[CH2:40][O:39][C:38]=3[CH:37]=[CH:36][C:35]=2[CH2:34][CH2:33]1>CN(C)C=O.O>[O:45]=[C:41]1[CH2:40][O:39][C:38]2[CH:37]=[CH:36][C:35]3[CH2:34][CH2:33][CH:32]([CH2:31][CH2:30][NH:29][C:24](=[O:28])[CH2:25][CH3:26])[C:44]=3[C:43]=2[NH:42]1

참가 물질

7

반응물 4

HCID 1032Propionic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 111281719-(2-aminoethyl)-1,7,8,9-tetrahydro-indeno[5,4-b][1,4]oxazin-2(3H)-one

생성물 1

HCID 11011664N-[2-(1,2,3,7,8,9-hexahydro-2-oxoindeno[5,4-b][1,4]oxazin-9-yl)ethyl]propionamide수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (372.0 mg, 1.9 mmol.) and 1-hydroxybenzotriazole monohydrate (257 mg, 1.9 mmol.) were suspended in N,N-dimethylformamide (2.5 mL). To the suspension was added, under ice-cooling, propionic acid (0.11 mL, 1.4 mmol.). This reaction mixture was stirred for one hour at room temperature, and, then, cooled again with ice, to which was added dropwise a solution of 9-(2-aminoethyl)-1,7,8,9-tetrahydroindeno[5,4-b][1,4] oxazin-2(3H)-one (300 mg, 1.3 mmol.) in N,N-dimethylformamide (1.5 mL). The mixture was stirred for one hour under ice-cooling. The reaction mixture was poured into water, and the organic matter was extracted with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1) to afford the title compound (yield 253.0 mg, 88%).

후처리

  1. additionTo the suspension was added, under ice-
  2. temperaturecooling
  3. temperaturecooled again with ice, to which
  4. stirringThe mixture was stirred for one hour under ice-
  5. temperaturecooling
  6. extractionthe organic matter was extracted with ethyl acetate
  7. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-20c669cf73d14579bb1faa9712b760f1
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06034239

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