(1,1'-Biphenyl)-3-carboxylic acid → HCID 67214341, compound

HRID 2421592Notes

Reaction equation

HRID 2421592 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1.CN(C=O)C>[CH:22]1([CH2:28][NH:29][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:14]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 65578Oxalyl chlorideHCID 76688Cyclohexanemethylamine

Product 1

HCID 67214341HCID 67214341, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. Cyclohexylmethylamine (325 μL, 2.5 mmol) was then added into half of the acid chloride solution at 0° C. The reaction mixture was then stirred at room temperature for 18 hours. The reaction mixture was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. Diethyl ether was added to the residue and a white solid precipitated which was collected by filtration and rinsed with a small amount of diethyl ether. The white solid was then dried under vacuum (115 mg, 78%). NMR 1H (ppm, CDCl3): 7.95 (s, 1H), 7.69 (d, J3=7.80 Hz, 2H), 7.59 (d, J3=8.22 Hz, 2H), 7.50-7.33 (m, 4H), 6.22 (br. s., 1H), 3.31 (t, J3=6.29 Hz, 2H), 1.80-1.53 (m, 6H), 1.31-1.10 (m, 3H), 1.05-0.84 (m, 2H).

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture was then stirred at room temperature for 18 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  6. washThe combined organic layers were washed with 2N HCl, saturated NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. additionDiethyl ether was added to the residue
  10. customa white solid precipitated which
  11. filtrationwas collected by filtration
  12. washrinsed with a small amount of diethyl ether
  13. customThe white solid was then dried under vacuum (115 mg, 78%)

Sources & evidence

ORD record
ord-32db8ab8d48c4231b1e9beed0b762133
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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