Reaktion #52973

Reaktionsgleichung

N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(hydroxymethyl)phenyl]-L-phenylalanine tert-butyl ester

triphenylphosphine

succinimide

DEAD

→

N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(succinimidomethyl)phenyl]-L-phenylalanine tert-butyl ester

Ausbeute 48.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to room temperature
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   SonstigeThe mixture was partitioned between H2O and EtOAc
4. 4
   Extraktionthe aqueous layer was extracted with EtOAC
5. 5
   TrocknenThe combined organic layer was dried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1)

Vorschrift

DEAD (0.13 mL) was added to an ice-cooled solution of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(hydroxymethyl)phenyl]-L-phenylalanine tert-butyl ester (250 mg), triphenylphosphine (175 mg) and succinimide (90 mg) in THF (3 mL) under N. The mixture was stirred at 0° C. for 30 min, and warmed to room temperature and stirred for 2 h. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was extracted with EtOAC. The combined organic layer was dried (MgSO4), and concentrated in vacuo. The residue was purified by preparative TLC (silica gel; eluent: EtOAc/hexane 1:1) to give N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(succinimidomethyl)phenyl]-L-phenylalanine tert-butyl ester (138 mg).

Quelle