Reaction #66939

ord-6ff94a40cbe94c12bb7d85c1cae3b3fd

Reaction equation

COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(-c2cc(OP(=O)(OCc3ccccc3)OCc3ccccc3)c3cc4c(cc3n2)OCO4)c1
167
COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(-c2cc(OP(=O)(OCc3ccccc3)OCc3ccccc3)c3cc4c(cc3n2)OCO4)c1
Dibenzyl 2-(3-([bis-[(benzyl)oxy]]phosphoryl)oxy-5-methoxyphenyl) -6,7-methylenedioxyquinolin-4-yl phosphate
→
COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(C2=Nc3cc4c(cc3C(=O)C2)OCO4)c1
168
Yield 45.0%
COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(C2=Nc3cc4c(cc3C(=O)C2)OCO4)c1
2-(3-([bis-[(benzyl)oxy]]phosphoryl)oxy-5-methoxyphenyl)-6,7-methylenedioxyquinolin-4-one
Yield 45.0%

Reactants

COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(-c2cc(OP(=O)(OCc3ccccc3)OCc3ccccc3)c3cc4c(cc3n2)OCO4)c1
167
COc1cc(OP(=O)(OCc2ccccc2)OCc2ccccc2)cc(-c2cc(OP(=O)(OCc3ccccc3)OCc3ccccc3)c3cc4c(cc3n2)OCO4)c1
Dibenzyl 2-(3-([bis-[(benzyl)oxy]]phosphoryl)oxy-5-methoxyphenyl) -6,7-methylenedioxyquinolin-4-yl phosphate

Reagents

None

Solvents

CO
methanol

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe precipitates were collected
  2. 2
    Otherpurified by column chromatography (SiO2, EtOAc)

Procedure

A suspension of 0.92 g (1.11 mmol) of 167 in 100 mL of methanol was stirred at 25° C. for 48 h. The precipitates were collected and purified by column chromatography (SiO2, EtOAc) to give 168.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524740B2uspto-grants-2013_09