1,2-Dichloroethane → 1-Benzyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepane

HRID 734321

Reaktionsgleichung

Reaktionsgleichung von HRID 734321
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:28]([CH:25]2[CH2:26][CH2:27][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:23][CH2:24]2)=[O:29])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 2283651-Benzyl-1,4-diazepaneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Produkt 1

HCID 603546031-Benzyl-4-(1-tert-butoxycarbonyl-piperidine-4-carbonyl)-[1,4]-diazepaneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Benzyl-[1,4]-diazepane (3.78 g) and 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (5.0 g) were dissolved in DCM (150 ml) and TEA (3.6 ml) was added followed by HOBT (1.34 g) and finally EDC (4.90 g). The reaction was stirred at rt overnight. The reaction mixture was then evaporated to a minimum, re-dissolved in DCM (50 ml) and washed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml). The organic layer was dried (MgSO4) and evaporated to a crude which was purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]. Fractions containing pure desired product were combined and evaporated to give the subtitled compound as a pale brown solid (7.1 g).

Aufarbeitung

  1. customThe reaction mixture was then evaporated to a minimum
  2. dissolutionre-dissolved in DCM (50 ml)
  3. washwashed with saturated sodium hydrogen carbonate solution (3×50 ml) and brine (50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to a crude which
  6. customwas purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]
  7. additionFractions containing pure desired product
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-32171a7d5ee746c5a0b602b6bdb50f56
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592347B2

Verknüpfte Notizen

Wird geladen…