4-Methylmorpholine → Boc-Ile-Pro-OBzl

HRID 973522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973522
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].CN1CCOCC1.C(OC(Cl)=O)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH:43]1[CH2:57][CH2:56][CH2:55][C@H:44]1[C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:43]1[CH2:57][CH2:56][CH2:55][C@H:44]1[C:45]([O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:46])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Komponenten

8

Edukt 6

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 2733413Proline benzyl ester hydrochloride

Produkt 1

HCID 14306235Boc-Ile-Pro-OBzlAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Boc-Ile-OH (12.01 g, 0.05 mole) in DMF (50 ml) was cooled to 0° C. and NMM (5.49 ml) was added. After cooling the solution to -15° C. isobutylchloroformate (6.48 ml) was added slowly while maintaining the temperature at -15° C. and stirred for 10 minutes at which time HOBt (7.65 g) was added and stirring was continued for additional 10 minutes. A pre-cooled solution of HCl-H-Pro-OBzl (12.09 g, 0.05 mole) in DMF (50 ml) and NMN (5.49 ml) was added to the above solution and the completeness of the reaction was followed by TLC. The reaction mixture was poured into a cold saturated NaHCO3 solution and stirred for one hour. The peptide was extracted into CHCl3 and washed with acid and base (0.5 N NaOH to remove HOBt), and on evaporating the solvent the product was obtained as an 92% yield. Rf1, 0.65. Anal. Calcd. for C23H34N2O5 : C 66.00, H 9.19, N 6.69%. Found: C 65.58, H 8.28, N 7.13%.

Aufarbeitung

  1. additionwas added slowly
  2. additionwas added
  3. stirringstirred for one hour
  4. extractionThe peptide was extracted into CHCl3
  5. washwashed with acid and base (0.5 N NaOH to remove HOBt)
  6. customon evaporating the solvent the product
  7. customwas obtained as an 92% yield

Quellen und Nachweise

ORD-Eintrag
ord-6aad5a2cf1c843bbb870535fd8f6f9ce
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064430

Notizen zur Reaktion

Wird geladen…