Triethylamine → [3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-L-tryptophan benzyl ester

HRID 1533284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533284
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:15](O)=[O:16])[N:10]=[C:9]1[CH2:27][CH2:28][CH2:29][CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:32]([O:39][C:40](=[O:53])[C@H:41]([CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=1)[NH2:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[CH2:32]([O:39][C:40](=[O:53])[C@H:41]([CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=1)[NH:42][C:15](=[O:16])[CH:14]([C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[CH:19]=1)[CH2:13][C:11]1[N:10]=[C:9]([CH2:27][CH2:28][CH2:29][CH3:30])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:12]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 220123253-(1-Tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionic acidHCID 45073232L-tryptophan benzyl ester hydrochloride

Produkt 1

HCID 54430710[3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-L-tryptophan benzyl esterAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionic acid (250 mg), L-tryptophan benzyl ester hydrochloride (209 mg) and triethylamine (128 mg) in N,N-dimethylformamide (5 ml) was added diphenylphosphoryl azide (198 mg) and the mixture was stirred at ambient temperature for 5.5 hours. The resulting mixture was diluted with ethyl acetate and the organic layer was washed successively with 0.5N hydrogen chloride aqueous solution, saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of the solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent; n-hexane:ethyl acetate=1:2) to give [3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-L-tryptophan benzyl ester (125 mg) as a yellow oil.

Aufarbeitung

  1. washthe organic layer was washed successively with 0.5N hydrogen chloride aqueous solution, saturated sodium bicarbonate aqueous solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of the solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (eluent; n-hexane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-6fdee13083e4439a93bc6e1663b97fa3
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207686B1

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