Triethylamine → (S)-N-CBZ-valinol

HRID 1636884

Reaktionsgleichung

Reaktionsgleichung von HRID 1636884
[NH2:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

Produkt 1

HCID 10900657(S)-N-CBZ-valinolAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of valinol (13.96 g, 0.14 mol) and triethylamine (18.87 mL, 0.14 mol) in 250 mL of dry methylene chloride cooled to 0° C. under a nitrogen atmosphere was added 19.3 mL (0.14 mol) of benzyl chloroformate dropwise over 20 min. After warming to RT overnight, the mixture was diluted with methylene chloride (100 mL) and washed with 1 N HCl (2×), brine and dried with anhydrous magnesium sulfate. The resulting mixture was filtered and evaporated to give 30.70 g (95.6%) of N-benzyloxycarbonyl-valinol as a white solid: Rf =0.27 (silica gel; 1:1 hexane:ethyl acetate). Used without further purification.

Aufarbeitung

  1. washwashed with 1 N HCl (2×), brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationThe resulting mixture was filtered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-549d03f5b8d84d3fb268b86ed2c583d9
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037325

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