Benzyloxycarbonyl-L-ornithine tert-butyl ester → tert-Butyl (2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoate

HRID 2379781

Reaktionsgleichung

Reaktionsgleichung von HRID 2379781
C(OC(=O)[C@H:7]([CH2:19][CH2:20][CH2:21][NH2:22])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(C)(C)C.[C:24]([O:31]C([O-])=O)(=O)[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[C:26]([O:25][C:24](=[O:31])[C@H:21]([CH2:20][CH2:19][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[NH:22][C:24]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:31])([CH3:29])([CH3:28])[CH3:27]

Komponenten

4

Edukt 2

HCID 15719252Benzyloxycarbonyl-L-ornithine tert-butyl esterHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 10047875tert-Butyl (2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Nδ -(Benzyloxycarbonyl-L-ornithine tert-butyl ester (7.50 g, 23.3 mmol) was dissolved in 27 ml of methylene chloride, and the solution was cooled to 0° C. To that solution was added dropwise tert-butyl pyrocarbonate (5.87 g, 26.9 mmol) in 10 ml of methylene chloride. The reaction mixture was stirred at 0° C. for 1 hour, and stirring was continued for 3 additional hours at room temperature. The solvent was evaporated at reduced pressure and the oily residue was chromatographed on a column of silica gel (25 cm×30 mm) using hexane:ethyl acetate (3:1) as solvent. Fractions of approximately 5 ml were collected, and those containing product were identified by thin layer chromatography (see below). Chromatographic fractions containing product were pooled and evaporated to a thick oil by rotary evaporation at reduced pressure. The yield was 8.63 gm (93.5%). 1H NMR (DCCl3) δ1.44 (s,9H), 1.46 (s,9H), 1.5-1.9 (m,4H), 3.23 (t,2H), 4.17 (t,1H), 4.88 (s,1H broad), 5.09 (s,2H and s,1H broad) 7.35 (s,5H).

Aufarbeitung

  1. stirringstirring
  2. customwas continued for 3 additional hours at room temperature
  3. customThe solvent was evaporated at reduced pressure
  4. customthe oily residue was chromatographed on a column of silica gel (25 cm×30 mm)
  5. customFractions of approximately 5 ml were collected
  6. additionChromatographic fractions containing product
  7. customevaporated to a thick oil by rotary evaporation at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fbac001cab2c40cc8fa21309660660e1
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05364881

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