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

HRID 413913

反応式

HRID 413913 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6033757c25e641f99fb5497413081c6e
出典データセット
uspto-grants-2003_05
特許番号
US06569890B2

関連ノート

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