Reaktion #1481179

Reaktionsgleichung

Boc-Thr-OH

bromoacetophenone

→

D3

Ausbeute 85.0%

N-tert-Butyloxycarbonylthreonine Phenacyl Ester

Ausbeute 85.0%

Lösungsmittel

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenAfter washing successively with aq HCl (200 ml, 0.1 N), H2O (100 ml), aq NaBCO3 (200 ml, 1 N) and brine (200 ml)
2. 2
   Trocknendrying (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigethe residue was triturated with Et2O
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe resulting solid was dried in the dark

Vorschrift

To a stirred suspension of Boc-Thr-OH (21.91 g, 0.1 mol) in EtOAc (200 ml) at 0° C., TEA (14 ml, 0.1 mol) and bromoacetophenone (19.0 g, 0.1 mol) were added. The reaction mixture was allowed to warm to 20° C., stirred for 2 days and then diluted with EtOAc (500 ml). After washing successively with aq HCl (200 ml, 0.1 N), H2O (100 ml), aq NaBCO3 (200 ml, 1 N) and brine (200 ml), drying (Na2SO4), filtered and concentrated in vacuo, the residue was triturated with Et2O and filtered. The resulting solid was dried in the dark to yield D3 (28.6 g, 85%). Rf=0.55 (hex-EtOAc 1:1, silica); M.p.=114.2° C.; [α]D22 −29.4 (c 2, EtOAc).

Quelle