Diphenylpropionic acid → N-Methoxy-N-methyl-3,3-diphenyl-propionamide

HRID 1617479Notes

Reaction equation

HRID 1617479 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([C:21]([O:25][N:26]1N=NC2C=CC=C[C:27]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNOC.C([O-])(O)=O.[Na+]>CN(C=O)C.CC(OC)(C)C.CCN(CC)CC>[CH3:21][O:25][N:26]([CH3:27])[C:9](=[O:10])[CH2:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 64798Diphenylpropionic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 54293842N-Methoxy-N-methyl-3,3-diphenyl-propionamideYield 84%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 3,3-diphenylpropionic acid ((CAS RN: [606-83-7]), 1.5 g) in DMF (17 mL) was added TBTU (3.0 g) and Et3N (2.8 mL) at 0° C. The reaction mixture was stirred at rt for 10 min and again was cooled down to 0° C. N,O-dimethylhydroxylamine hydrochloride (0.78 g) was added and the mixture was stirred at rt for 2 days. A saturated solution of NaHCO3 and TBME were added, the phases were separated and the inorganic one was extracted with TBME. The combined organic layers were washed with 1M KHSO4 followed by brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield the title compound as a light brown oil (1.5 g, 84%), MS (ESI+): m/z=270.2 ([M+H]+).

Workup

  1. temperatureagain was cooled down to 0° C
  2. stirringthe mixture was stirred at rt for 2 days
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with TBME
  5. washThe combined organic layers were washed with 1M KHSO4
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

Sources & evidence

ORD record
ord-a61d75a2d0474386af3a5ab05e2152a2
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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