Citric Acid → HCID 86753303, compound

HRID 355575Notes

Reaction equation

HRID 355575 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CS(C)=O.C(N([CH2:16][CH3:17])CC)C.[C:18](O)(=O)[CH2:19][C:20](CC(O)=O)([C:22](O)=O)O.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>C(Cl)Cl>[CH2:35]([O:34][CH2:33]/[CH:16]=[CH:17]\[CH2:2][CH:1]=[O:5])[C:31]1[CH:32]=[CH:22][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 65578Oxalyl chloride

Product 1

HCID 86753303HCID 86753303, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

The compound resulting from Example 17A in THF is added dropwise to a -70° C. solution containing oxalyl chloride, DMSO and methylene chloride. After addition, the mixture is stirred 45 minutes at -70° C., then added dropwise, maintaining the internal temperature below -50° C., triethylamine in methylene chloride. The mixture is then warmed to 0° C. and 10% citric acid is added. The layers are separated and the organic layer is washed with 10% sodium bicarbonate and 10% sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. additionis added dropwise to a -70° C. solution
  2. additionAfter addition
  3. additionadded dropwise
  4. temperatureThe mixture is then warmed to 0° C.
  5. customThe layers are separated
  6. washthe organic layer is washed with 10% sodium bicarbonate and 10% sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-735794df33a348ae8f601035b6152c1d
Source dataset
uspto-grants-1998_11
Patent number
US05831115

Reaction notes

Loading…