4-Methylmorpholine → L-Proline, 1-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-L-alanyl]-, 2-(ethoxycarbonyl)-2-methylhydrazide

HRID 437134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437134
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20](O)=[O:21])=[O:17])[CH3:15])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:41]([O:43][C:44](=[O:48])[N:45]([CH3:47])[NH2:46])[CH3:42]>O1CCCC1.C(Cl)(Cl)Cl>[CH2:41]([O:43][C:44](=[O:48])[N:45]([CH3:47])[NH:46][C:20](=[O:21])[C@@H:19]1[CH2:23][CH2:24][CH2:25][N:18]1[C:16](=[O:17])[C@H:14]([CH3:15])[NH:13][C:11](=[O:12])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:42]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11217246N-methylethoxycarbohydrazideHCID 11902955Boc-ala-ala-pro-OH

Produkt 1

HCID 54384473L-Proline, 1-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-L-alanyl]-, 2-(ethoxycarbonyl)-2-methylhydrazide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.009 moles of t-butyloxycarbonylalanylalanylproline in 80 ml of dry tetrahydrofuran which has been cooled to -20° to -30° is added 1.0 ml of N-methylmorpholine and 1.2 ml of isobutylchloroformate. After stirring for 10 minutes there is added 0.009 moles of 2-azaalanine ethyl ester in 50 ml of chloroform. The reaction mixture is stirred overnight at room temperature and then concentrated in vacuo. The residue is taken up between ethyl acetate and 0.25 N hydrochloric acid. The organic layer is separated, washed with saturated sodium bicarbonate solution, water, dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel. Elution with ethyl acetate gives t-butyloxycarbonylalanylalanylprolyl-2-azaalanine ethyl ester.

Aufarbeitung

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. concentrationconcentrated in vacuo
  3. customThe organic layer is separated
  4. washwashed with saturated sodium bicarbonate solution, water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel
  8. washElution with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-713c9d0d52ed4bb69d1a807f085c58a0
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029772

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