p-Toluenesulfonic acid monohydrate → HCID 14541574, compound

HRID 1464021Notes

Reaction equation

HRID 1464021 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][C:32]([O:34][CH2:35][CH3:36])=[O:33])(=O)C.[OH2:37].[C:38]1([CH3:48])[CH:43]=[CH:42][C:41](S(O)(=O)=O)=[CH:40][CH:39]=1>C(O)C>[CH2:48]([O:37][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:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:17]([CH3:30])[C:16]=3[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:7]([CH2:8][CH3:9])[C:3]=2[CH2:1][CH3:2])=[C:16]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:17]=1[CH3:30])=[O:21])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 109095633,4-DiethylpyrroleHCID 14541573HCID 14541573, compound

Product 1

HCID 14541574HCID 14541574, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Diethylpyrrole (Sessler, J. L.; Mozaffari, A.; Johnson, M. R. submitted to Organic Syntheses) (7) (0.62 g, 5.0 mmol), benzyl 5-(acetoxymethyl)-3-ethoxycarbonylmethyl-4-methylpyrrole-2-carboxylate (10) (3.94 g, 10.6 mmol), and p-toluenesulfonic acid monohydrate (152 mg) were dissolved in 50 ml of absolute ethanol and heated at reflux for 4 hours under N2. 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 CH2Cl2 /ethanol to afford compound 11 as a fine, off-white powder (2.13 g, 50%); m.p. 127°-128° C.; 1H NMR (CDCl3) delta 1.28 (6 H, t, J=7.47 HZ, CH2CH3), 1.20 (6 H, t, J=7.07 Hz, OCH2CH3), 2.26 (6 H, s, CH3), 2.48 (4 H, q, J=7.34 HZ, CH2CH3), 3.31 (4 H, s, CH2CO2Et), 3.70 (4 H, s, pyrrole2 -CH2), 4.05 (4 H, q, J=7.09 Hz, OCH2CH3), 4.75 (4 H, br s, CH2Ph), 7.14-7.32 (10 H, m, aromatic), 8.83 (1 H, s, NH), 11.5 (2 H, br s, NH); CIMS, (M+H)+ 778.6; HRMS, 749.3689 (calcd for C44H51N3O8 : 749.3676).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours under N2
  3. waitplaced in the freezer for several hours
  4. filtrationThe product was then collected by filtration
  5. washwashed with a small amount of cold ethanol
  6. customrecrystallized from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-77937cf41d8a4e128e5c7b7e4693dca6
Source dataset
uspto-grants-1994_04
Patent number
US05302714

Reaction notes

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