tert-Butyl cyanoacetate → Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate

HRID 1767369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767369
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=O)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[NH:23][C@H:24]([CH:34]=O)[C:25](=C=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(C)(C)C.[C:36]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])#[N:37].[C:46]([O-:49])(=[O:48])C.[NH4+:50]>COCCOC>[NH2:37][C:36]1[NH:50][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:34]([CH:24]([NH:23][C:46]([O:49][C:2]([CH3:7])([CH3:3])[CH3:1])=[O:48])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:38]=1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

Komponenten

6

Edukt 4

HCID 70693tert-Butyl cyanoacetateHCID 517165Ammonium AcetateHCID 5205131-[2-(Benzyloxy)phenyl]ethan-1-oneHCID 86604947N-tert-butoxy-carbonyl-phenylalaninal

Produkt 1

HCID 22258838Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylateAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of the starting compound 1A (3.000 g, 13.258 mmol), N-tert-butoxy-carbonyl-phenylalaninal (3.305 g, 13.258 mmol), tert-butyl cyanoacetate (1.872 g, 13.258 mmol), ammonium acetate (3.066 g, 39.774 mmol) and 1,2-dimethoxyethane (5.0 mL) was heated at reflux for 6 hrs. After cooled to room temperature, the mixture was extracted with ethyl acetate and saturated NaHCO3 solution. The separated organic phase was washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with diisopropyl ether to give tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate as a yellow solid (1.281 g, yield; 16%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate and saturated NaHCO3 solution
  4. washThe separated organic phase was washed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-66f6518548ac41a2b2220e9731489a0e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232909B2

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