1-Oxo-3,4-dihydro-2H-1lambda~5~-pyrrole → Ethyl 2-[2-butyl-3,4-dihydro-4-oxo-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-6-quinazolinyl]hexahydro-pyrrolo[1,2-b]isoxazole-3-carboxylate

HRID 486510Notes

Reaction equation

HRID 486510 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]=[CH:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[N+:60]1([O-:65])[CH2:61][CH2:62][CH2:63][CH:64]=1>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]3[O:65][N:60]4[CH2:61][CH2:62][CH2:63][CH:64]4[CH:54]3[C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 3001481-Oxo-3,4-dihydro-2H-1lambda~5~-pyrroleHCID 54221423Ethyl 3-[2-butyl-3,4-dihydro-4-oxo-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-6-quinazolinyl]-2-propenoate

Product 1

HCID 18958919Ethyl 2-[2-butyl-3,4-dihydro-4-oxo-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-6-quinazolinyl]hexahydro-pyrrolo[1,2-b]isoxazole-3-carboxylateYield 53.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.300 g of ethyl 3-[2-butyl-3,4-dihydro-4-oxo-3-[[2'-[l-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-6-quinazolinyl]-2-propenoate in 20 ml of toluene is added 0.293 g of 3,4-dihydro-2H-pyrrole 1-oxide and the reaction mixture heated at reflux for 6 hours. The reaction mixture is cooled and concentrated in vacuo to a residue which is purified by chromatography on silica reaction mixture heated at reflux for 6 hours. The reaction mixture is cooled and concentrated in vacuo to a residue which is purified by chromatography on silica gel by elution with 1:1 ethyl acetate-hexanes to give 0.177 g of the desired product. FAB MASS SPEC 620 (M+H, --Ph3c).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated in vacuo to a residue which
  5. customis purified by chromatography on silica reaction mixture
  6. temperatureheated
  7. temperatureat reflux for 6 hours
  8. temperatureThe reaction mixture is cooled
  9. concentrationconcentrated in vacuo to a residue which
  10. customis purified by chromatography on silica gel by elution with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-66b1f1454f2d4335ad16ed78afb433db
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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