Cumylamine → (R)-N2-(Boc)-N5-(Cbz)-N-(1-methyl-1-phenylethyl)ornithine amide

HRID 366049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366049
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[C:36]([NH2:45])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([CH3:38])[CH3:37]>C(Cl)Cl>[C:14]([NH:13][C@@H:12]([C:11]([NH:45][C:36]([CH3:38])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:37])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Komponenten

4

Edukt 2

HCID 68509CumylamineHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester

Produkt 1

HCID 131722052(R)-N2-(Boc)-N5-(Cbz)-N-(1-methyl-1-phenylethyl)ornithine amideAusbeute 109,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 4(b) above from Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (5.0 g; 11.5 mmol; see Example 4(a) above) and cumylamine (1.55 g; 11.5 mmol) and 160 mL of CH2Cl2. The reaction mixture was heated to reflux for 2 hours. The mixture was concentrated to dryness and dissolved in EtOAc and washed with saturated aqueous KHSO4 and brine, dried with Na2SO4, filtered and concentrated to give 6.1 g of the sub-title compound as a yellow oil.

Aufarbeitung

  1. customPrepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. concentrationThe mixture was concentrated to dryness
  5. dissolutiondissolved in EtOAc
  6. washwashed with saturated aqueous KHSO4 and brine
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b9b2e7d5d75b4e8783dd62e532f94f45
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127414

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