Water → N-tert-butoxycarbonyl-D-valine (R)-alpha-methylthiomethylbenzylamide

HRID 618956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618956
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:17][S:18][CH2:19][C@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.O.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:17][S:18][CH2:19][C@H:20]([NH:27][C:13](=[O:15])[C@@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 5

HCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 70345754(R)-alpha-methylthiomethylbenzylamine hydrochloride

Produkt 1

HCID 54474124N-tert-butoxycarbonyl-D-valine (R)-alpha-methylthiomethylbenzylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-tert-butoxycarbonyl-D-valine (2.39 g, 11.0 mmols) and 10.0 mmols of the above-obtained (R)-α-methylthiomethylbenzylamine hydrochloride were dissolved in 60 ml of methylene chloride. Triethylamine (1.53 ml, 11.0 mmols), 2.11 g (11.0 mmols) of water-soluble carbodiimide hydrochloride and 1.49 g (11.0 mmols) of HOBt were added to the solution while being cooled to 0° C. The mixture was stirred for 1 hour while being cooled, and then overnight at room temperature. After the reaction mixture was concentrated under reduced pressure, 100 ml of water were added to the residue, and the solution was extracted twice with 100 ml of ethyl acetate. The organic layer was washed twice with a 5% citric acid aqueous solution, with 50 ml of a saturated aqueous solution of sodium chloride, twice with a 5% sodium hydrogencarbonate aqueous solution and with 50 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain N-tert-butoxycarbonyl-D-valine (R)-α-methylthiomethylbenzylamide as a solid in a quantitative yield.

Aufarbeitung

  1. temperaturewhile being cooled
  2. customovernight
  3. customat room temperature
  4. concentrationAfter the reaction mixture was concentrated under reduced pressure, 100 ml of water
  5. additionwere added to the residue
  6. extractionthe solution was extracted twice with 100 ml of ethyl acetate
  7. washThe organic layer was washed twice with a 5% citric acid aqueous solution, with 50 ml of a saturated aqueous solution of sodium chloride, twice with a 5% sodium hydrogencarbonate aqueous solution and with 50 ml of a saturated aqueous solution of sodium chloride
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-98ab52507c5646c6a524b387ea4c9977
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958496

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