Hydrochloric Acid → HCID 14802668, Verbindung

HRID 65598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65598
Cl.N(OCCC(C)C)=O.[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:24]([NH:26][C@H:27]([C:36]([N:38]=[N+]=[N-])=[O:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:25])[CH2:22][OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:54])[CH3:53])[NH:46][C:47](=[O:50])[CH2:48]N>O1CCCC1.C(N(CC)CC)C.CN(C)C=O>[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:53])[CH3:54])[NH:46][C:47](=[O:50])[CH2:48][NH:38][C:36](=[O:37])[C@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:26][C:24](=[O:25])[C@H:21]([CH2:22][OH:23])[NH:20][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 13751932methyl (2S)-2-(2-aminoacetamido)-4-methylpentanoate hydrochlorideHCID 54294707N-benzyloxycarbonyl-L-seryl-L-tyrosyl azide

Produkt 1

HCID 14802668HCID 14802668, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a stirred solution of 7.49 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosyl hydrazide [this compound is reported in Helv. Chim. Acta, 41, 1852 (1958)] in 50 ml. of N,N-dimethylformamide, cooled to -30° C., is first added 16.9 ml. of 3.607 N hydrogen chloride in tetrahydrofuran and then 2.7 ml. of isoamyl nitrite, and the resulting mixture is stirred at -30° C. for 30 minutes. The mixture, which contains N-benzyloxycarbonyl-L-seryl-L-tyrosyl azide, is next cooled to -60° C., and to it are added first 8.57 ml. of triethylamine, then 4.297 g. of glycyl-L-leucine methyl ester hydrochloride and finally 2.52 ml. more of triethylamine. The stirred mixture is allowed to warm to 0° C. during one hour and is stirred at 0° C. for one hour and kept at -5° C. for 48 hours. It is then filtered, and the filtrate is evaporated under reduced pressure at 40°-50° C. The gummy residue is partitioned between dilute hydrochloric acid and ethyl acetate, and the organic layer is separated, washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride, dried, and evaporated to give a solid residue of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycyl-L-leucine methyl ester; m.p. 166°-167° C., following two crystallizations from ethyl acetate-ether; [α]D25 -25.4° (2% in N,N-dimethylformamide); [α]D25 -38.2° (2.09% in methanol).

Aufarbeitung

  1. additionto it are added first 8.57 ml
  2. temperatureto warm to 0° C. during one hour
  3. waitkept at -5° C. for 48 hours
  4. filtrationIt is then filtered
  5. customthe filtrate is evaporated under reduced pressure at 40°-50° C
  6. customThe gummy residue is partitioned between dilute hydrochloric acid and ethyl acetate
  7. customthe organic layer is separated
  8. washwashed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride
  9. customdried
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5f8374911abc4e3eb30bcfdb09930e6c
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128540

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