Dicyclohexylamine → BOC-Nva-Met-OMe

HRID 851721

Reaktionsgleichung

Reaktionsgleichung von HRID 851721
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH2:3][CH2:4][CH3:5].C1CCC(NC2CCCCC2)CC1.[NH2:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34].Cl.C(N(CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)(Cl)Cl>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:29][C@H:30]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:8])[CH2:3][CH2:4][CH3:5]

Komponenten

7

Edukt 5

HCID 7582DicyclohexylamineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2733748(2S)-2-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 11435579L-Methionine, methyl ester, hydrochloride

Produkt 1

HCID 57129312BOC-Nva-Met-OMeAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

BOC-Nva-OH, liberated from 4.78 g (12 mmoles) of the DCHA salt as described in Step 1 of Example 4, and 2.6 g (13 mmoles) of H-Met-OMe.HCl are dissolved in 40 ml of chloroform, and 1.82 ml (13 mmoles) of triethylamine are added. The mixture is cooled with ice, and a solution of 2.58 g (12.5 mmoles) of DCC in 20 ml of chloroform is added under stirring. The reaction mixture is allowed to stand at 5° C. overnight, thereafter the separated DCU is filtered off. The filtrate is washed thrice with 20 ml of n hydrochloric acid, each, thrice with 20 ml of n sodium hydrocarbonate solution, each, and then with 20 ml of water, dried over anhydrous sodium sulfate, and evaporated. The oily residue is crystallized from petroleum ether, and the resulting 3.42 g of crude product is recrystallized from a mixture of ethyl acetate and petroleum ether. 3.08 g (71%) of BOC-Nva-Met-OMe are obtained; m.p.: 69°- 70° C., Rf2 =0.81, [α]D25 =-42.7° (c=1%, in methanol).

Aufarbeitung

  1. temperatureThe mixture is cooled with ice
  2. filtrationthe separated DCU is filtered off
  3. washThe filtrate is washed thrice with 20 ml of n hydrochloric acid
  4. dry with materialeach, thrice with 20 ml of n sodium hydrocarbonate solution, each, and then with 20 ml of water, dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe oily residue is crystallized from petroleum ether
  7. customthe resulting 3.42 g of crude product is recrystallized from a mixture of ethyl acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a436c9f484834bf091c7315974f2dd90
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386073

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