Felbinac → HCID 11087289, compound

HRID 2185453Notes

Reaction equation

HRID 2185453 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)[CH2:21][CH3:22])C.[C:25]1([C:35]2[CH:40]=[CH:39]C=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:28](CC(O)=O)=[CH:27][CH:26]=1.[CH3:41][C:42]([OH:45])([CH3:44])[CH3:43]>>[C:42]([O:45][C:23]([NH:20][CH2:21][C:22]1[CH:37]=[CH:36][C:35]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:40][CH:39]=1)=[O:8])([CH3:44])([CH3:43])[CH3:41]

Participants

5

Reactant 4

HCID 3332FelbinacHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 11087289HCID 11087289, compound

Procedure

Diphenylphosphoryl azide (1.12 mL) and triethylamine (789 μl) were added to a solution of 4-biphenylylacetic acid (1.00 g) in 2-methyl-2-propanol (20 mL). The mixture was refluxed for 13 hr and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 1 N hydrochloric acid, water, saturated sodium hydrogen carbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (489 mg) as yellow crystals: 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 4.36 (d, J=5.4 Hz, 2H), 4.87(br s, 1H), 7.26-7.27, 7.32-7.45 and 7.55-7.58 (each m, total 9H).

Workup

  1. temperatureThe mixture was refluxed for 13 hr
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 1 N hydrochloric acid, water, saturated sodium hydrogen carbonate, and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5da3b5057c0e4ca986b5db5bcf768fd1
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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