Water → 2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin

HRID 1789819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789819
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23]Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1([CH3:35])[O:31][C:30](=[O:32])[CH:29]([CH3:33])[C:28](=[O:34])[O:27]1.C(N(CC)CC)C.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C:29]2([CH3:33])[C:28](=[O:34])[O:27][C:26]([CH3:25])([CH3:35])[O:31][C:30]2=[O:32])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 772992,2,5-Trimethyl-1,3-dioxane-4,6-dioneHCID 220360092-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin

Produkt 1

HCID 220361342-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridinAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

2-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin (1.6 g, 4.0 mmol) was added to a solution of 2,2,5-trimethyl-1,3-dioxane-4,6-dione (630 mg, 4.0 mmol) and triethylamine (0.58 mL, 4.2 mmol) in dimethyl sulfoxide (40 mL). The reaction mixture was stirred overnight and water (100 mL) was added. The mixture was extracted with EtOAc, the combined organic phases washed with water and brine and dried. Concentration under reduced pressure gave crude 2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin (2.06 g)

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic phases washed with water and brine
  3. customdried
  4. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9eb117af31054614bd2029b09386dfab
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071175B1

Notizen zur Reaktion

Wird geladen…