Methanol → HCID 59216483, compound

HRID 2245701Notes

Reaction equation

HRID 2245701 reaction equation
[F:1][CH:2]([F:26])[C:3]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[N:11](CC2C=CC(OC)=CC=2)[CH2:10][CH2:9]3)[CH2:5][CH2:4]1.C(OC(=O)C)C.CO>C(O)(C(F)(F)F)=O>[F:26][CH:2]([F:1])[C:3]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[NH:11][CH2:10][CH2:9]3)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 59216394HCID 59216394, compound

Product 1

HCID 59216483HCID 59216483, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

Compound (VII) (0.068 g, 0.19 mmole) was dissolved in TFA 1 ml and heated to 70° C. for 1.5 hours. To the reaction mixture cooled to room temperature was added ethylacetate and the solution was washed with brine followed by sodium bicarbonate 5% solution, and again with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel prep TLC with 5% methanol in dichloromethylene affording compound (VIII) 0.030 g, 66% yield.

Workup

  1. temperatureTo the reaction mixture cooled to room temperature
  2. washthe solution was washed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8895f00aad834f89a926d108ea770aff
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

Loading…