p-Toluenesulfonic acid → 2,5-Bis(5-benzyloxycarbonyl-3-ethyl-4-methylpyrrol-2-ylmethyl)-3,4-diethylpyrrole

HRID 3094Notes

Reaction equation

[CH2:1]([C:3]1[C:7]([CH2:8][CH3:9])=[CH:6][NH:5][CH:4]=1)[CH3:2].C(O[CH2:14][C:15]1[NH:19][C:18]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[C:17]([CH3:30])[C:16]=1[CH2:31][CH3:32])(=O)C.[C:33]1([CH3:43])[CH:38]=[CH:37][C:36](S(O)(=O)=O)=[CH:35][CH:34]=1>C(O)C>[CH2:43]([O:22][C:20]([C:18]1[NH:19][C:15]([CH2:14][C:4]2[NH:5][C:6]([CH2:14][C:15]3[NH:19][C:18]([C:20]([O:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[O:21])=[C:17]([CH3:30])[C:16]=3[CH2:31][CH3:32])=[C:7]([CH2:8][CH3:9])[C:3]=2[CH2:1][CH3:2])=[C:16]([CH2:31][CH3:32])[C:17]=1[CH3:30])=[O:21])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3,4-Diethylpyrrole (2A, FIG. 2)28 (0.6, 4.9 mmol), benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate (2B, FIG. 2)29 (2.5 g, 7.9 mmol), and p-toluenesulfonic acid (0.15 g) were dissolved in 60 mL of absolute ethanol and heated at 60° C. for 8 h under nitrogen. The resulting suspension was reduced in volume to 30 mL and placed in the freezer for several hours. The product was then collected by filtration, washed with a small amount of cold ethanol, and recrystallized from dichloromethane-ethanol to afford a white powder (2.07 g, 82%): mp 211° C. NMR spectra and high resolution mass spectral data were obtained as described and are reported 13a.

Workup

waitplaced in the freezer for several hours
filtrationThe product was then collected by filtration
washwashed with a small amount of cold ethanol
customrecrystallized from dichloromethane-ethanol

Sources & evidence

ORD record: ord-83eb8c4f8a924307bcc393ec98b1dc0e
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733903

Reaction notes

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