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(R,S)-Benzyl 5-(1-Hydroxyethyl)-1H-pyrrole-2-carboxylate
 
 
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Short Note

N-[5-(3-Phenylpropionyl)-1H-pyrrole-2-carbonyl]-L-proline Methyl Ester

Department of Chemistry, The University of Canterbury, Private Bag 4800, Christchurch, New Zealand
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(3), M338; https://doi.org/10.3390/M338
Submission received: 22 February 2003 / Accepted: 22 May 2003 / Published: 1 June 2003
Molbank 2003 m338 i001
To a stirring solution of the pyrrole carboxylic acid 1 [1] (100 mg, 0.41 mmol, 1 equiv) and L-proline methyl ester hydrochloride (75 mg, 0.45 mmol, 1.1 equiv) in dry dichloromethane (6 mL) at r.t. under an inert atmosphere were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (102 mg, 0.53 mmol, 1.3 equiv) and 1-hydroxybenzotriazole hydrate (83 mg, 0.62 mmol, 1.5 equiv) [2].
N,N-Diisopropylethylamine (Hünig's base, 58 mg, 0.45 mmol, 1.1 equiv) was added, and the reaction mixture was stirred at r.t. for 16 h. The solution was then diluted with dichloromethane (10 mL), washed with 3 M hydrochloric acid (2 × 10 mL), water (2 × 10 mL), and the combined aqueous washings were back-extracted with dichloromethane (2 × 10 mL). The combined organic fractions were dried (MgSO4) and the solvent was removed by evaporation under reduced pressure. Flash chromatography on silica (ethyl acetate/petroleum ether, 2:1) afforded the title compound 2 (100 mg, 69%) as a tan solid.
mp 84-86°C.
IR (KBr, diffuse refraction method) 1539.1, 1598.9, 1660.6, 1737.7, 2954.7, 3028.0, 3435.0.
1H NMR (CDCl3, 500 MHz) d 2.03-2.27 (m, 4H, NCH2CH2CH2CH), 3.03 (m, 2H, PhCH2CH2), 3.11 (m, 2H, PhCH2CH2), 3.75 (s, 3H, CO2CH3), 3.84 (m, 1H, NCH2aCH2CH2CH), 3.96 (m, 1H, NCH2bCH2CH2CH), 4.68 (q, 1H, J = 4.1 Hz, NCH2CH2CH2CH), 6.61 (m, 1H, pyrrole H3), 6.82 (m, 1H, pyrrole H4), 7.17-7.29 (m, 5H, ArH), 10.10 (s (br), 1H, pyrrole NH).
13C NMR (CDCl3, 75 MHz) d 25.3, 28.6 (NCH2CH2CH2CH), 30.3 (PhCH2CH2), 40.1 (PhCH2CH2), 48.4 (NCH2CH2CH2CH), 52.4 (CO2CH3), 60.2 (NCH2CH2CH2CH), 112.9 (pyrrole C3), 115.4 (pyrrole C4), 126.2, 128.3, 128.5, 140.9 (ArC), 129.5 (pyrrole C2), 132.5 (pyrrole C5), 159.6 (CON), 172.5 (CO2), 189.9 (CH2CO).
HRMS (M+) Calcd for C20H22N2O4: 354.1580. Found: 354.1583.
Anal. Calcd for C20H22N2O4: C, 67.78; H, 6.26; N, 7.90. Found: C, 67.75; H, 6.51; N, 7.97.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Martyn, D. C.; Abell, A. D. J. Chem. Soc., Org. Biomol. Chem. in press.
  2. Tian, Z-Q.; Brown, B. B.; Mack, D. P.; Hutton, C. A.; Bartlett, P. A. J. Org. Chem. 1997, 62, 514.
  • Sample availability: available from the authors.

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MDPI and ACS Style

Martyn, D.C.; Abell, A.D. N-[5-(3-Phenylpropionyl)-1H-pyrrole-2-carbonyl]-L-proline Methyl Ester. Molbank 2003, 2003, M338. https://doi.org/10.3390/M338

AMA Style

Martyn DC, Abell AD. N-[5-(3-Phenylpropionyl)-1H-pyrrole-2-carbonyl]-L-proline Methyl Ester. Molbank. 2003; 2003(3):M338. https://doi.org/10.3390/M338

Chicago/Turabian Style

Martyn, Derek C., and Andrew D. Abell. 2003. "N-[5-(3-Phenylpropionyl)-1H-pyrrole-2-carbonyl]-L-proline Methyl Ester" Molbank 2003, no. 3: M338. https://doi.org/10.3390/M338

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