tert-Butyl acetate → N5-benzyloxycarbonyl-ornithine, t-butyl ester

HRID 128722

Reaktionsgleichung

Reaktionsgleichung von HRID 128722
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.Cl(O)(=O)(=O)=O>O>[C:24]([O:18][C:17](=[O:19])[C@H:15]([CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[NH2:16])([CH3:27])([CH3:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 7009570H-Orn(Z)-OH

Produkt 1

HCID 7019766N5-benzyloxycarbonyl-ornithine, t-butyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Nδ -(Benzyloxycarbonyl)-L-ornithine tert-butyl ester was prepared according to a general published procedure (Bodanszky, M.; Bodanszky, A.; The Practice of Peptide Synthesis; Spring Verlag: New York, 1984). Specifically, Nδ -(benzyloxycarbonyl)-L-ornithine (10.0 gm, 37.6 mmol, Sigma Chemicals, Inc.) was mixed with tert-butyl acetate (564 ml) and perchloric acid (5.91 ml, 69-72% aqueous solution) at room temperature. The reaction mixture became homogenous after 15 minutes and was stirred at room temperature for 2 days. Water (300 ml) was added to the reaction mixture, and the two layers obtained were separated. The organic layer was extracted twice (2×200 ml) with water, and the combined aqueous layers were adjusted to pH 9.5-10.0 with 50% NaOH. The aqueous layer was then filtered to remove a small amount of insoluble material, and the filtrate was extracted with ethyl acetate (3×300 ml). The combined ethyl acetate extracts were dried over MgSO4 and were concentrated by rotary evaporation at reduced pressure to yield 7.5 g of Nδ -(benzyloxycarbonyl)-L-ornithine tert-butyl ester as an oil (65% yield). 1H NMR (DCCl3) δ 1.44 (s,9H), 1.5-1.9 (m,4H), 3.23 (t,2H), 3.31 (t,1H), 5.09 (s,2H and s,1H broad), 7.35 (s,5H) .

Aufarbeitung

  1. customNδ -(Benzyloxycarbonyl)-L-ornithine tert-butyl ester was prepared
  2. customthe two layers obtained
  3. customwere separated
  4. extractionThe organic layer was extracted twice (2×200 ml) with water
  5. filtrationThe aqueous layer was then filtered
  6. customto remove a small amount of insoluble material
  7. extractionthe filtrate was extracted with ethyl acetate (3×300 ml)
  8. dry with materialThe combined ethyl acetate extracts were dried over MgSO4
  9. concentrationwere concentrated by rotary evaporation at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec5f47754f41437bb625afc3c6bbf808
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464858

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