Triethylamine → HCID 54264483, Verbindung

HRID 1768913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768913
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].Cl.[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH2:32])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:34])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[C:30](=[O:33])[CH2:31][NH:32][S:13]([C:8]1[C:9]2[C:4](=[C:3]([N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:15])=[O:14])([CH3:22])([CH3:20])[CH3:21]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 57383535tert-Butyl glycyl-L-prolinate--hydrogen chloride (1/1)

Produkt 1

HCID 54264483HCID 54264483, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Dimethylamino-l-naphthalenesulfonyl chloride (5.10 g, 18.9 mmol) was added in portions to a well-stirred solution of glycyl-L-proline tert-butyl ester hydrochloride (5.00 g, 18.9 mmol) and triethylamine (5.20 mL, 37.8 mmol) in dry tetrahydrofuran (175 mL). The mixture was stirred at room temperature for 4 hours before it was diluted with ethyl acetate and washed successively with saturated sodium bicarbonate solution and brine. Following drying and solvent evaporation, the residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes) and furnished 7.62 g (87%) of the title compound as a fluorescent green foam, m.p. 60°-67° C.; 1H NMR (CDCl3) δ 8.51 (dd, J=8.5, 3.3 Hz, 1H), 8.30 (d, J=8.7 Hz, 1H), 8.21-8.16 (m, 1H), 7.58-7.43 (m, 2H), 7.15 (d, J=7.4 Hz, 1H), 5.85-5.79 (m, 1H), 4.27-4.23 (m, 1H), 3.76-3.62 (m, 2H), 3.48-3.21 (m, 2H), 2.84 (s, 6H), 2.10-1.75 (m, 4H), 1.33 and 1.32 (2s, 9H); 13C NMR (CDCl3) ppm 170.84, 170.45, 165.84, 165.46, 152.04, 134.31, 134.16, 130.79, 130.16, 130.12, 129.87, 129.52, 129.47, 128.77, 123.23, 123.17, 119.22, 119.13, 115.59, 83.00, 81.82, 59.99, 59.38, 46.97, 45.98, 45.64, 44.69, 44.58, 31.41, 29.13, 28.05, 27.96, 24.49, 23.80, 22.36; IR (KBr, cm-1) 3266, 2978, 2942, 2876, 2834, 1736, 1658, 1456, 1440, 1370, 1330, 1148, 792, 626, 574; MS m/z (MH+) calcd 461.1984, obsd 461.1982.

Aufarbeitung

  1. washwashed successively with saturated sodium bicarbonate solution and brine
  2. customFollowing drying
  3. customsolvent evaporation
  4. customthe residue was chromatographed on silica gel (gradient elution with first 40% ethyl acetate in hexanes followed by 50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0744f8bbf9a747d19cc35affc60c72c1
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380713

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