Hydrochloric Acid → Z-Lys(Boc)-Lys(Boc)-Pro-NH2

HRID 328757

Reaktionsgleichung

Reaktionsgleichung von HRID 328757
[NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([NH:33]N)=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.N(OCCC(C)C)=O.N1[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56]([NH2:58])=[O:57].C(N(CC)CC)C>O1CCOCC1.CN(C)C=O>[NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([N:33]1[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56]([NH2:58])=[O:57])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 8471Triethylamine2×HCID 111306L-ProlinamideHCID 131710715Z-Lys(Boc)-Lys(Boc)-NHNH2

Produkt 1

HCID 131710716Z-Lys(Boc)-Lys(Boc)-Pro-NH2

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of compound XIII (1.25 g, 2 mmoles) in dimethylformaide (8 ml) is chilled to -40° C to -50° C in a Dry-ice-acetone bath and 3.66M hydrogen chloride in dioxane (1.37 ml) is added. To this is then added dropwise isoamyl nitrite (0.29 ml, 2.2 mmoles) and the mixture is stirred at -10° C to -20° for 10 minutes. The mixture is again chilled to -40° C to -50° C and an ice-cold solution of XIV (0.30 g, 2 mmoles) and triethylamine (1.1 ml, 7.7 mmoles) in dimethylformamide (10 ml) is introduced. The temperature is allowed to rise to 0° C, at which the mixture is stirred for 3 hours. After the pH have been adjusted to about 8 with an additional quantity of triethylamine (0.27 ml, 2 mmoles) the reaction mixture is kept at 4° C for 2 days. The solvent is removed by evaporation in vacuo at a bath temperature of 40° C. The resulting residue is dissolved in ethyl acetate and the solution is washed with ice-cold M hydrochloric acid and M sodium bicarbonate, dried over magnesium sulfate and evaporated in vacuo. Repeated precipiration of the residue obtained above yields the desired tripeptide XV; yield 1.29 g (91%), mp. 85°-90° C, [α]D22 - 40.5°±0.4° (c 2.0, methanol).

Aufarbeitung

  1. temperatureThe mixture is again chilled to -40° C to -50° C
  2. customto rise to 0° C, at which
  3. stirringis stirred for 3 hours
  4. waitis kept at 4° C for 2 days
  5. customThe solvent is removed by evaporation in vacuo at a bath temperature of 40° C
  6. dissolutionThe resulting residue is dissolved in ethyl acetate
  7. washthe solution is washed with ice-cold M hydrochloric acid and M sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customobtained

Quellen und Nachweise

ORD-Eintrag
ord-6a2f7d01b50440dd884691738d15853a
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018753

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