Dimethylformamide → 1-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanol

HRID 489031

Reaktionsgleichung

Reaktionsgleichung von HRID 489031
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:34][C:35]([OH:39])([CH3:38])[CH2:36]O.CN(C=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:34][C:35]([CH3:38])([OH:39])[CH3:36])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 684102-Methylpropane-1,2-diolHCID 726987N-Carbobenzoxy-L-valine

Produkt 1

HCID 540342421-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanolAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

N-Benzyloxycarbonyl-L-valine (2.02 g, 8.0 mmol), 4-dimethylaminopyridine (100 mg, 0.8 mmol), and), and dicyclohexylcarbodiimide (2.04 g, 9.9 mmol, is 20 mL CH2Cl2) were added to 2-methyl-1,2-propanediol (12.2 mmol) in 30 mL dry CH2Cl2, with cooling in an ice bath. DMF (5 mL) was added. After stirring for 5 h at 10° C., the reaction mixture was filtered, concentrated, and then redissolved in ethyl acetate. The organic solution was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated. Flash column chromatography (silica, 2/1 petroleum ether-ethyl acetate) gave 2.3 g of the title compound.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionredissolved in ethyl acetate
  5. washThe organic solution was washed with saturated NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-99783b6fb4d54fcf9e08d10e8ed010ff
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974802B2

Verknüpfte Notizen

Wird geladen…