1,2-Dichloroethane → Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({(4S)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentyl}amino)carbonyl]butyl}carbamate

HRID 269679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269679
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([OH:26])=O)[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32](=[O:41])[NH:33][C@H:34]([CH2:39][OH:40])[CH2:35][CH2:36][CH2:37][NH2:38])([CH3:30])([CH3:29])[CH3:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:24]([NH:38][CH2:37][CH2:36][CH2:35][C@H:34]([NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:41])[CH2:39][OH:40])=[O:26])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7350734Z-Ndelta-Boc-L-ornithineHCID 88986916HCID 88986916, Verbindung

Produkt 1

HCID 86625287Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({(4S)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentyl}amino)carbonyl]butyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under argon, 0.155 g (0.42 mmol) of N2-[(benzyloxy)carbonyl]-N5-(tert-butoxycarbonyl)-L-ornithine and 0.12 g (0.55 mmol) of tert-butyl[(1S)-4-amino-1-(hydroxymethyl)butyl]carbamate (Example 247A) are dissolved in 6 ml of dimethylformamide. Then, at 0° C. (ice bath), 0.105 g (0.55 mmol) of EDC and 0.017 g (0.13 mmol) of HOBt are added. The mixture is slowly warmed to RT and stirred at RT for 12 h. The solution is concentrated in vacuo and the residue is taken up with ethyl acetate. The organic phase is washed successively with saturated sodium bicarbonate and sodium chloride solutions, dried over magnesium sulfate and evaporated in vacuo. The remaining solid is purified by preparative HPLC (Kromasil, mobile phase acetonitrile/0.25% aqueous trifluoroacetic acid 5:95→95:5).

Aufarbeitung

  1. concentrationThe solution is concentrated in vacuo
  2. washThe organic phase is washed successively with saturated sodium bicarbonate and sodium chloride solutions
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe remaining solid is purified by preparative HPLC (Kromasil, mobile phase acetonitrile/0.25% aqueous trifluoroacetic acid 5:95→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-b9091529bc9440bca5e74681b4ce68fc
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446102B2

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