Sodium Hydroxide → 5-Propylcarbamoyl-biphenyl-3-carboxylic acid

HRID 2421620Notes

Reaction equation

HRID 2421620 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:11]([C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH3:17])[CH:12]=1)=[O:6]>CO.CC(C)=O.O.Cl>[CH2:15]([NH:14][C:13]([C:11]1[CH:12]=[C:7]([C:5]([OH:6])=[O:4])[CH:8]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1)=[O:18])[CH2:16][CH3:17]

Participants

7

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67214482HCID 67214482, compound

Product 1

HCID 672136885-Propylcarbamoyl-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of NaOH (44 mg, 1.1 mmol) in 372 μL of MeOH was added to a solution of 68D (284 mg, 0.96 mmol) in 1.8 mL of acetone. The reaction was stirred at room temperature for 16 hrs after which time 10 mg of NaOH and 200 μL of MeOH were added. The reaction was stirred for 72 hrs. The reaction mixture was then concentrated in vacuo and the residue obtained was dissolved in water and a few drops of concentrated HCl were added till pH ˜1. An off-white solid appeared. It was collected by filtration and extensively rinsed with water. The solid was then dried in vacuo (194 mg, 72%). NMR 1H (ppm, CD3OD): 8.43 (t., J4=1.63 Hz, 1H), 8.38 (t., J4=1.73 Hz, 1H), 8.27 (t., J4=1.78 Hz, 1H), 7.71-7.67 (m, 2H), 7.48 (m, 2H), 7.39 (t.t., J3=7.34 Hz, J4=1.36 Hz 1H), 3.39-3.34 (m, 2H), 1.65 (sext., J3=7.18 Hz, 2H), 0.98 (t., J3=7.34 Hz, 3H).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue obtained
  4. filtrationIt was collected by filtration
  5. washextensively rinsed with water
  6. customThe solid was then dried in vacuo (194 mg, 72%)

Sources & evidence

ORD record
ord-4ac2da28136a482f8a83934926045470
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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