1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Leu-Gly-OBzl

HRID 256496

Reaktionsgleichung

Reaktionsgleichung von HRID 256496
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].O.C1C=CC2N(O)N=NC=2C=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH:39]1[CH:44]=[CH:43][C:42]([CH2:45][O:46][C:47]([CH2:49][NH2:50])=[O:48])=[CH:41][CH:40]=1.CCN=C=NCCCN(C)C>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]([NH:50][CH2:49][C:47]([O:46][CH2:45][C:42]1[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=1)=[O:48])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 12373896N-Boc-L-Leucine Hydrate

Produkt 1

HCID 13242213BOC-Leu-Gly-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of 6.00 g of BOC-Leu-OH.H2O, 3.49 g of HOBT and 9.59 of H-Gly-OBzl.TosOH dissolved in 30 ml of DMF, under cooling at -5° C. and stirring, a solution of 4.97 ml of WSC dissolved in 10 ml of DMF was added dropwise, and after one hour, the temperature was regulated to room temperature, at which stirring was continued overnight. The reaction mixture was concentrated under reduced pressure to evaporate DMF, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed successively with 1N hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 9.2 g of BOC-Leu-Gly-OBzl as oily product. Rf1 =0.59.

Aufarbeitung

  1. additionwas added dropwise
  2. customwas regulated to room temperature, at which
  3. stirringstirring
  4. waitwas continued overnight
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customto evaporate DMF
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe ethyl acetate layer was washed successively with 1N hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2f8afd9897194a1885a558ecbd9bcb00
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04703106

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