4-(4-Aminophenyl)butanoic acid → 4-[4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid

HRID 2235823Notes

Reaction equation

HRID 2235823 reaction equation
[C:1]1([C:7](=O)[CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:23][CH:22]=1>C(O)(=O)C>[CH3:11][C:10]1[N:20]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:25][CH:26]=2)[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][C:9]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 270494-(4-Aminophenyl)butanoic acidHCID 131847311,3-Diphenylpentane-1,4-dione

Product 1

HCID 247974694-[4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A soln of 1,3-diphenyl-pentane-1,4-dione (104 mg; 0.412 mmol) and 4-(4-amino-phenyl)-butyric acid (89 mg; 0.497 mmol) in acetic acid (2 mL) was heated at 120° C. After 6 h, the reaction was concentrated on a rotary evaporator. Ethyl acetate (5 mL) was added and this washed with H2O (1×2 mL) and satd NaCl (1×3 mL). The organic portion was dried (MgSO4) and filtered through silica with an EtOAc wash. Crude product was adsorbed onto silica (0.3 g) then purified by MPLC (12 g of silica using a 0→50% EtOAc in hexanes gradient). Pure product was obtained as a white solid (115 mg; 71%). 1H NMR (CDCl3) δ 7.54-7.49 (m, 2H), 7.44-7.38 (m, 2H), 7.26-7.07 (m, 10H), 6.56 (s, 1H), 2.72 (t, J=7.6 Hz, 2H), 2.40 (t, J=7.4 Hz, 2H), 2.25 (s, 3H), 2.00 (m, 2H); LC-MS (ESI−) 394 ([M−H]−).

Workup

  1. concentrationthe reaction was concentrated on a rotary evaporator
  2. additionEthyl acetate (5 mL) was added
  3. washthis washed with H2O (1×2 mL) and satd NaCl (1×3 mL)
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered through silica with an EtOAc
  6. washwash
  7. customthen purified by MPLC (12 g of silica using a 0→50% EtOAc in hexanes gradient)
  8. customPure product was obtained as a white solid (115 mg; 71%)

Sources & evidence

ORD record
ord-1be8b1e2984040019704f78488e1b97c
Source dataset
uspto-grants-2010_05
Patent number
US07714022B2

Reaction notes

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