Trifluoroacetic acid → (R)-2-(4-Methoxybenzoylamino)-2-phenylethylazide

HRID 1826599Notes

Reaction equation

HRID 1826599 reaction equation
[C:1]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][N:11]=[N+:12]=[N-:13])([O:3]C(C)(C)C)=O.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].C(Cl)(=O)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1>O1CCOCC1.O>[CH3:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([C:1]([NH:8][C@H:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][N:11]=[N+:12]=[N-:13])=[O:3])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7477p-Anisoyl chlorideHCID 11430Potassium CarbonateHCID 20790081HCID 20790081, compound

Product 1

HCID 53998160(R)-2-(4-Methoxybenzoylamino)-2-phenylethylazideYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

(R)-2-(Boc-amino)-2-phenylethyl azide (47.8 g, 0.182 mole) was added to trifluoroacetic acid (500 mL) with stirring and ice-water bath cooling. The cooling bath was removed, the reaction was allowed to stir 1 h, and the solvent was removed in vacuo at 35° C. water bath temperature. The residue was co-evaporated with toluene to give a weight of 75.0 g. The residue was dissolved in 1,4-dioxane (500 mL) and water (500 mL), with ice-water bath cooling, and then potassium carbonate (113.5 g, 0.82 mol), and anisoyl chloride (37.3 g, 0.219 mol) were added. Another portion of 1,4-dioxane (300 mL) was added to facilitate stirring. After stirring over the weekend, water (1 L) was added. The mixture was cooled to −15° C., and vacuum filtered to collect a white solid. The solid was washed with water, air dried, and then dried under vacuum at 50° C. for 4 h to afford 46.3 g (86%) of the title compound.

Workup

  1. temperatureice-water bath cooling
  2. customThe cooling bath was removed
  3. stirringto stir 1 h
  4. customthe solvent was removed in vacuo at 35° C. water bath temperature
  5. customto give a weight of 75.0 g
  6. stirringto facilitate stirring
  7. additionwas added
  8. filtrationvacuum filtered
  9. customto collect a white solid
  10. washThe solid was washed with water, air
  11. customdried
  12. customdried under vacuum at 50° C. for 4 h

Sources & evidence

ORD record
ord-dae57145bba94c4487bbac54e8d9ef9d
Source dataset
uspto-grants-2006_05
Patent number
US07053078B2

Reaction notes

Loading…