p-Toluenesulfonic acid → 2-Methyl-1-(3-nitrobenzyl)-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

HRID 842201

반응식

HRID 842201 반응식
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])([O-:4])=[O:3].C(=O)(O)[O-].[Na+].[N+](C1C=C(C=CC=1)CN)([O-])=O.[CH2:29]([O:31][C:32](=[O:46])[CH:33]([CH2:37][C:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:34](=O)[CH3:35])[CH3:30].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(OCC)C>[CH2:29]([O:31][C:32]([C:33]1[CH:37]=[C:38]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:9]([CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)[C:34]=1[CH3:35])=[O:46])[CH3:30]

참가 물질

8

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 1227223-NitrobenzylamineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoateHCID 516892Sodium BicarbonateHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)

생성물 1

HCID 99471922-Methyl-1-(3-nitrobenzyl)-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

m-Nitrobenzylamine hydrochloride (3 g) was suspended in an aqueous solution of saturated sodium bicarbonate (30 mL), then extracted with chloroform. The organic layer was dried over MgSO4, the solids separated and solvents removed under vacuum to yield the free base. The m-nitrobenzylamine (5 mmol, 0.8 g) prepared above, 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The residue was resuspended in ethyl ether, and the benzylamine tosic acid salt was filtered from the mixture. The filtrate was concentrated under vacuum, and the resulting oil purified over silica to yield the named product, 1H-NMR (CDCl3, ppm): 1.24 t (3H), 2.36 s (3H), 4.07-4.30 q (2H), 5.11 s (2H), 6.58 s (1H), 6.98-7.44 bm (7H), 7.69 bs (1H) , 7.97 bd (1H).

후처리

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solids separated
  4. customsolvents removed under vacuum
  5. customto yield the free base
  6. temperatureheated
  7. temperatureunder reflux
  8. filtrationthe benzylamine tosic acid salt was filtered from the mixture
  9. concentrationThe filtrate was concentrated under vacuum
  10. customthe resulting oil purified over silica
  11. customto yield the named product, 1H-NMR (CDCl3, ppm): 1.24 t (3H), 2.36 s (3H), 4.07-4.30 q (2H), 5.11 s (2H), 6.58 s (1H), 6.98-7.44 bm (7H), 7.69 bs (1H) , 7.97 bd (1H)

출처 및 근거

ORD 기록
ord-7e584c90846840d293a88e52f74878ec
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372777B1

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