Reaktion #1004083

Reaktionsgleichung

N-Boc-L-tyrosine methyl ester

benzenesulfonyl chloride

triethylamine

→

N-Boc-O-benzenesulfonyl-L-tyrosine methyl ester

Ausbeute 100.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction mass was washed with 5% hydrochloric acid (7.3 g) and 5% aqueous sodium bicarbonate (8.4 g)
2. 2
   Einengenconcentrated under reduced pressure with a rotary evaporator

Vorschrift

N-Boc-L-tyrosine methyl ester 3 (3.0 g, 0.01 mol) and benzenesulfonyl chloride (1.8 g, 0.01 mol) were dissolved in toluene (14.8 g) and then cooled to 0° C. To the mixture was added dropwise triethylamine (1.0 g, 0.01 mol) at 0° C. over 35 min. The mixture was further kept at 0° C. for 3 hrs. The reaction mass was washed with 5% hydrochloric acid (7.3 g) and 5% aqueous sodium bicarbonate (8.4 g) and then concentrated under reduced pressure with a rotary evaporator to give N-Boc-O-benzenesulfonyl-L-tyrosine methyl ester 5 (4.35 g, yield 100%) as white solid.

Quelle