Triethylamine → N-(5-phthalimidopentanoyl)-L-alanyl-D-isoglutamine benzyl ester

HRID 439308

Reaktionsgleichung

Reaktionsgleichung von HRID 439308
Cl.[CH2:2]([O:9][C:10](=[O:23])[CH2:11][CH2:12][C@H:13]([C:20](=[O:22])[NH2:21])[NH:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH2:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:24]1(=[O:41])[N:28]([CH2:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[C:27](=[O:36])[C:26]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:25]12.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:2]([O:9][C:10](=[O:23])[CH2:11][CH2:12][C@H:13]([C:20](=[O:22])[NH2:21])[NH:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH:17][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[C:24](=[O:41])[C:25]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:26]2[C:27]1=[O:36])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17149185-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentanoic acidHCID 12873810benzyl L-alanyl-D-isoglutaminate hydrochloride

Produkt 1

HCID 22860846N-(5-phthalimidopentanoyl)-L-alanyl-D-isoglutamine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

L-alanyl-D-isoglutamine benzyl ester hydrochloride (548 mg, 1.6 mmoles) and 5-phthalimidopentanoic acid (400 mg, 1.6 mmoles) were dissolved in N,N-dimethylformamide (8 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (495 mg, 1.8 mmoles) and triethylamine (323 mg, 3.2 mmoles) were added thereto. The reaction mixture was stirred for 1 hour at 0° C. and for 24 hours at room temperature. The reaction mixture was diluted by ethyl acetate (40 ml) and the organic phase was washed successively with citric acid (0.52M; 3×10 ml), water (3×10 ml), saturated NaCl solution (3×10 ml), saturated NaHCO3 solution (3×10 ml), water (3×10 ml) and saturated NaCl solution (3×10 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the product was precipitated from n-hexane/diethyl ether. The compound was filtered off and crystallized from acetone.

Aufarbeitung

  1. washthe organic phase was washed successively with citric acid (0.52M; 3×10 ml), water (3×10 ml), saturated NaCl solution (3×10 ml), saturated NaHCO3 solution (3×10 ml), water (3×10 ml) and saturated NaCl solution (3×10 ml)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customthe product was precipitated from n-hexane/diethyl ether
  6. filtrationThe compound was filtered off
  7. customcrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-7a25c840ab3f425a85ddf6761c65a1d6
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514654

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