Reaktion #714376

Reaktionsgleichung

MS-4

MS-4

(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Intermediate 172

(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate

acetaldoxime

MeOH

→

(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solid was filtered
2. 2
   Waschenwashed with deionized H2O and acetone
3. 3
   FiltrationThe solid was filtered
4. 4
   Waschenwashed with MeOH
5. 5
   Sonstigethe filtrate was evaporated
6. 6
   Sonstigeto afford crude product

Vorschrift

4 Å molecular sieves (MS-4 Å) were impregnated with the corresponding metal salt (CuCl2-2H2O) as follows: 1 mmol of the salts was dissolved in 100 ml of deionized H2O and stirred with 1 g of MS-4 Å at room temperature for 6 h. The solid was filtered, washed with deionized H2O and acetone, and dried in an oven at 150° C. for 1 h. (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(cyanomethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 172, 3.60 g, 5.78 mmol), Cu(II)Cl2-4 Å catalyst (200 mg), acetaldoxime (1.762 mL, 28.90 mmol, 5.0 eq) and MeOH (40.0 mL) were stirred at 60° C. for 15 h. The solid was filtered, washed with MeOH and the filtrate was evaporated to afford crude product.

Quelle