4-Methylmorpholine → HCID 178501375, Verbindung

HRID 1395813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1395813
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH3:30][O:31][C:32](=[O:64])[C@H:33]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)[NH:34][C:35](=[O:55])[C@H:36]([CH:52]([CH3:54])[CH3:53])[NH:37][C:38](=[O:51])[C@H:39]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:50])[NH2:49])[NH:40][N+:41]([O-:43])=[O:42]>C(Cl)Cl>[CH3:30][O:31][C:32](=[O:64])[C@H:33]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=1)[NH:34][C:35](=[O:55])[C@H:36]([CH:52]([CH3:54])[CH3:53])[NH:37][C:38](=[O:51])[C@H:39]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:49])[NH2:50])[N:40]([C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[N+:41]([O-:43])=[O:42]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 178501377HCID 178501377, Verbindung

Produkt 1

HCID 178501375HCID 178501375, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

8.84 g of t-butoxycarbonylsarcosine is dissolved in 200 ml of methylene chloride. 10.5 ml of N-methylmorpholine is added to the solution. The solution is cooled to -70° C. 6.1 ml of isobutyl chloroformate is then added. The reaction mixture is warmed up to -15° C. and stirred for 5 minutes. The reaction mixture is again cooled to -70° C. 25.5 g of nitroarginylvalyltyrosine methyl ester hydrochloride is added to the reaction mixture. The reaction mixture is allowed to warm to room temperature, and then is stirred for 16 hours. The reaction mixture is extracted three times with 0.5 M potassium bisulfate and once with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The residue is dissolved in 200 ml of ethyl ether. The ether solution is added to cold rapidly stirring Skellysolve B. The white precipitate is filtered and dried to afford the product t-butoxycarbonylsarcosylnitroarginylvalyltyrosine methyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture is warmed up to -15° C.
  2. temperatureThe reaction mixture is again cooled to -70° C
  3. temperatureto warm to room temperature
  4. stirringis stirred for 16 hours
  5. extractionThe reaction mixture is extracted three times with 0.5 M potassium bisulfate
  6. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. dissolutionThe residue is dissolved in 200 ml of ethyl ether
  9. additionThe ether solution is added to cold rapidly stirring Skellysolve B
  10. filtrationThe white precipitate is filtered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1032476ff95445a4b3070184f5257448
Quelldatensatz
uspto-grants-1980_05
Patentnummer
US04204991

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