Reaktion #2045899

Reaktionsgleichung

(R)-benzyl 3-amino-4-(dimethylamino)butanoate

triethylamine

6-phenoxypyridine-3-sulfonyl chloride

→

title compound

Ausbeute 37.0%

(R)-benzyl 4-(dimethylamino)-3-(6-phenoxypyridine-3-sulfonamido)butanoate

Ausbeute 37.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvents were removed in vacuo
2. 2
   Sonstigethe residue was purified by preparatory HPLC
3. 3
   workup.DISSOLUTIONThe residue was dissolved into CH2Cl2 (50 mL)
4. 4
   Waschenwashed with 0.1 N NaOH (5 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated

Vorschrift

To a solution of (R)-benzyl 3-amino-4-(dimethylamino)butanoate (32 mg, 0.086 mmol), triethylamine (50 μL, 0.36 mmol) and DMAP (1 mg, 0.008 mmol) in anhydrous CH2Cl2 (1 mL) was added 6-phenoxypyridine-3-sulfonyl chloride is reacted with R-aminocarnitine benzyl ester (67 mg, 0.25 mmol). The solution was stirred overnight at room temperature. The solvents were removed in vacuo and the residue was purified by preparatory HPLC. The residue was dissolved into CH2Cl2 (50 mL) and washed with 0.1 N NaOH (5 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (18 mg, 37%). MS ESI 470.2 [M+H]+, calcd for [C24H27N3O5S+H]+ 470.17.

Quelle