Isobutyl chloroformate → HCID 178512905, Verbindung

HRID 1679645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679645
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].C(OC(N([N+]([O-])=O)[C@H](C(O)=O)CCCNC(=N)N)=O)(C)(C)C.C(Cl)(=O)OCC(C)C.[NH2:43][CH2:44][C:45]([NH2:47])=[O:46]>CN(C)C=O.O1CCCC1.C(N(CC)CC)C>[NH2:1][C@H:2]([C:10]([NH:43][CH2:44][C:45]([NH2:47])=[O:46])=[O:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Komponenten

8

Edukt 4

HCID 62365Isobutyl chloroformateHCID 69020GlycinamideHCID 178418600HCID 178418600, VerbindungHCID 178454196HCID 178454196, Verbindung

Produkt 1

HCID 178512905HCID 178512905, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Protected arginine, i.e., tert-butyloxycarbonylnitro-arginine is dissolved in a suitable solvent such as dimethylformamide and tetrahydrofuran. The dissolved protected amino acid is then cooled to a temperature slightly below the freezing point (0° C), whereupon isobutyl chlorocarbonate and triethylamine is added with stirring. After a short period, glycinamide dissolved in dimethylformamide is added. The mixture is then permitted to warm to room temperature and stirred for a period of several hours and then filtered. The filtrate is recovered and evaporated to dryness and then extracted with dimethylformamide. The dimethylformamide solution is precipitated with ethylacetate to yield the dipeptide, i.e., protected arginyl-glycinamide.

Aufarbeitung

  1. additionis added
  2. waitAfter a short period
  3. additionis added
  4. stirringstirred for a period of several hours
  5. filtrationfiltered
  6. customThe filtrate is recovered
  7. customevaporated to dryness
  8. extractionextracted with dimethylformamide
  9. customThe dimethylformamide solution is precipitated with ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-55a5380ecac242509ecaf254a4a52585
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04081533

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