Reacción #61309

Ecuación de reacción

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

Disolventes

MeOH

THF

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente