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

HRID 2259935Notes

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. 2A)28 (0.6 g, 4.9 mmol), benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate (2B, FIG. 2A)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-10285bafc2da4ed081bcdfc6668d9a50
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05475104

Reaction notes

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