Reaction #46320

ord-c58c4d2699ab4fa7bc11164dc9ec05bd

Reaction equation

Cl
HCl
CCCC(=O)O[C@@H]1[C@H](O)c2c(cc(OC)c3c(=O)c4cc5ccccc5nc4n(C)c23)OC1(C)C
compound
CCCC(=O)O[C@@H]1[C@H](O)c2c(cc(OC)c3c(=O)c4cc5ccccc5nc4n(C)c23)OC1(C)C
(±)-cis 1-Hydroxy-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl butyrate
→
CCCC(=O)OC1=Cc2c(cc(OC)c3c(=O)c4cc5ccccc5nc4n(C)c23)OC1(C)C
6-Methoxy-3,3,14-trimethyl-7-oxo-7,14-dihydro-3H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl butyrate

Reactants

—
solution
Cl
HCl
CCCC(=O)O[C@@H]1[C@H](O)c2c(cc(OC)c3c(=O)c4cc5ccccc5nc4n(C)c23)OC1(C)C
compound
CCCC(=O)O[C@@H]1[C@H](O)c2c(cc(OC)c3c(=O)c4cc5ccccc5nc4n(C)c23)OC1(C)C
(±)-cis 1-Hydroxy-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl butyrate

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherdried
  2. 2
    Concentrationconcentrated under reduced pressure
  3. 3
    Otherto be isolated

Procedure

Add 4 drops of a 10% solution of HCl to a solution of 0.29 mmol of the compound of Example 13 in 6 ml of dichloromethane. The reaction mixture is stirred for 3 days at ambient temperature and then dried and concentrated under reduced pressure. Chromatography of the residue on silica gel (dichloromethane/methanol gradient) allows the expected product to be isolated.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741325B2uspto-grants-2010_06