Réaction #61309

Équation de réaction

H7

(rac.)-(1R*,5S*)-7-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

DIPEA

acetyl chloride

HCl dioxane

→

(rac.)-(1R*,5S*)-3-Acetyl-7-[4-(2-hydroxyethoxy)phenyl]-3,9-diazabicyclo-[3.3.1]non-6-ene-6,9-dicarboxylic acid 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

Solvants

MeOH

THF

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutrePurification of the residue by FC (EtOAc/heptane 1:1→EtOAc MeOH/EtOAc 1:9)

Mode opératoire

As for compound S1, from H7 (5.80 g, 7.73 mmol), CH2Cl2 (60 mL), 4M HCl/dioxane (60 mL), THF (50 mL), DMAP (47 mg, 0.384 mmol), DIPEA (5.29 mL, 31.7 mmol), acetyl chloride (0.604 mL, 8.08 mmol), and MeOH (5 mL). Purification of the residue by FC (EtOAc/heptane 1:1→EtOAc MeOH/EtOAc 1:9) led to the title compound (3.07 g, 69%). Rf=0.20 (EtOAc). LC-MS: Rt=4.80; ES+: 576.93.

Source