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Ethylmorpholine → N-((Phenylmethoxy)carbonyl)-L-alanyl-L-alanine

HRID 47039
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 47039
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CC[O:22]CC1)C.C(Cl)(=O)C(C)(C)C.Br.C(N[C:36](=[O:40])[C@H:37]([CH3:39])[NH2:38])C>O1CCCC1.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:38][C@H:37]([C:36]([OH:40])=[O:22])[CH3:39])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7525Ethylmorpholine2×HCID 62493Pivaloyl chlorideHCID 736104N-carbobenzyloxyalanineHCID 86736706L-alanine ethylamide hydrobromide

Produkt 1

HCID 7009583N-((Phenylmethoxy)carbonyl)-L-alanyl-L-alanine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

7.5 g (0.034 mol) of N-benzyloxycarbonyl-L-alanine were dissolved in 50 ml of dry tetrahydrofuran and the solution was cooled to -5° C. 4.26 ml (0.034 mol) of N-ethylmorpholine and 4.14 ml (0.034 mol) of pivaloyl chloride were then added and the solution was stirred at -5° C. for 30 minutes. To this mixture was then added a solution of 7.0 g (0.034 mol) of L-alanine ethylamide hydrobromide in 50 ml of dimethylformamide followed by 8.5 ml (0.068 mol) of N-ethylmorpholine. The solution was stirred at -10° C. for 1 hour and then left to stand for 16 hours at room temperature. The solvents were removed by evaporation; the product crystallising on the addition of water. The yield of N-benzyloxycarbonyl-L-alanyl-L-alanine obtained was 9.05 g (83%); melting point 203°-205° C.; [α]D20 =-1.1° (c=1.02% in dimethylformamide; [α] 36520 =-9.2° (c=1.02% in dimethylformamide).

Aufarbeitung

  1. stirringThe solution was stirred at -10° C. for 1 hour
  2. waitleft
  3. waitto stand for 16 hours at room temperature
  4. customThe solvents were removed by evaporation
  5. customthe product crystallising on the addition of water

Quellen und Nachweise

ORD-Eintrag
ord-ffe30715d2234adfab12f8449f2baa6b
Quelldatensatz
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04176116

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