Nitrogen → 3-Acetylbenzeneacetic acid

HRID 1189408Notes

Reaction equation

HRID 1189408 reaction equation
N#N.C([O:7][C:8](=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2([CH3:21])OCC[O:17]2)[CH:11]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[C:16]([C:12]1[CH:11]=[C:10]([CH2:9][C:8]([OH:22])=[O:7])[CH:15]=[CH:14][CH:13]=1)(=[O:17])[CH3:21]

Participants

4

Reactant 2

HCID 947NitrogenHCID 67128531HCID 67128531, compound

Product 1

HCID 117886053-Acetylbenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid tert-butyl ester (268 mg, 0.96 mmol) in TFA (3.89 mL) was stirred for 45 min at rt. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (25 mL) and 1N NaOH (10 mL). The layers were separated and the aq. layer was acidified with 1N HCl and extracted twice with CH2Cl2 (25 mL). The combined org. layers were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 02: tR=0.73 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 (25 mL) and 1N NaOH (10 mL)
  3. customThe layers were separated
  4. extractionextracted twice with CH2Cl2 (25 mL)
  5. dry with materiallayers were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-515ba2ff714b4035a71c3cce27cab403
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…