Reaktion #42336

Reaktionsgleichung

3-[(1-propylbutyl)sulfonyl]alanine

N-Cbz succinamide

→

N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine

Ausbeute 109.5%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 250 ml round bottom flask equipped with magnetic stir bar and N2 inlet
2. 2
   workup.ADDITION6.9 g NMK was added dropwise
3. 3
   Temperaturto warm to room temperature
4. 4
   Sonstigereaction
5. 5
   EinengenThe reaction was concentrated in vacuo
6. 6
   Sonstigepartitioned between ethyl acetate and 1 N HCl
7. 7
   WaschenThe organic layer was washed with water, brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   Einengenconcentrated in vacuo

Vorschrift

A 250 ml round bottom flask equipped with magnetic stir bar and N2 inlet was charged with 7.8 g (27 mmole) 3-[(1-propylbutyl)sulfonyl]alanine and 7.4 g (30 mmole) N-Cbz succinamide in 100 ml methylene chloride. The reaction was cooled to 0° C., and 6.9 g NMK was added dropwise. The reaction was allowed to warm to room temperature and stirred for 4 hours at which point HPLC analysis indicated complete reaction. The reaction was concentrated in vacuo and partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give 11.4 g of N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine that was used without further purification. M+H=386.

Quelle