methyl 5-bromo-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]benzoate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 5-bromo-2-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]oxy}benzoate (Preparation 70) (8.92 g, 23.8 mmmol) in DCM (18 ml) was treated with TFA (7 ml) and stirred for 5 hrs. Additional (2 ml) TFA was added and the reaction left overnight. The solvent was evaporated, re-evaporated with toluene (5×) and dissolved in toluene (50 ml). The resulting residue was treated with triethylamine (4 equiv) and heated at 100° C. overnight then evaporated. The residue was purified by flash chromatography twice eluting with 50% EtOAc/hexane then 40-45% EtOAc/hexane. The fractions were evaporated to give the title compound (3.4 g) as a white solid. MS (ES): C9H881BrNO2 requires 243; found 244 [M+H]+. the reaction left overnight The solvent was evaporated re-evaporated with toluene (5×) dissolved in toluene (50 ml) then evaporated The residue was purified by flash chromatography twice eluting with 50% EtOAc/hexane The fractions were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DIAD (9.62 g, 47.6 mmol) was added to a mixture of methyl 5-bromo-2-hydroxybenzoate (10 g, 43.3 mmol), 1,1-dimethylethyl (2-hydroxyethyl)carbamate (6.98 g, 43.3 mmol) and triphenylphosphine (12.47 g, 47.6 mmol) in THF (250 ml) and stirred at RT for 2.5 hr. Additional triphenylphosphine (2.5 g) was added followed by DIAD (4 ml) and the mixture left standing overnight. Evaporation and purification by flash chromatography eluting with 25% EtOAc/hexane gave the title compound as a yellow oil (8.92 g). MS (ES): C15H2081BrNO5 requires 375; found 276 [M+H−100]+. the mixture left standing overnight Evaporation and purification by flash chromatography eluting with 25% EtOAc/hexane