Benzocaine → HCID 22056518, compound

HRID 1829997Notes

Reaction equation

HRID 1829997 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9]C)=[O:7])=[CH:4][CH:3]=1.[C:13]1([CH:19]2[CH2:24][C:23](=[O:25])[O:22][C:20]2=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC#N>CC(O)C>[CH3:9][O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([NH:1][C:20](=[O:21])[CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:24][C:23]([OH:25])=[O:22])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6342AcetonitrileHCID 136911Phenylsuccinic Anhydride

Product 1

HCID 22056518HCID 22056518, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ethyl 4-aminobenzoate (910 mg, 5.50 mmol) and phenyl succinic anhydride (1070 mg, 6.00 mmol) were dissolved in 40 mL abs. CH3CN and stirred overnight at r.t. The solid precipitate was isolated and digirated with 2-propanol, dried in vacuum, dissolved in DCM and washed with citric acid. 4-{[4-(methoxycarbonyl)-phenyl]amino}-4-oxo-3-phenylbutanoic acid was isolated as a crystalline solid (980 mg, 2.88 mmol). M.p. 212° C.; TLC (cyclohexane/EtOAc 7/3) Rf 0.17; 1H NMR (400 MHz, D6-DMSO) δ 1.39 (t, J=7.2 Hz, 3H); 2.75 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 3.42 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 4.09 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 4.35 (q, J=7.2 Hz, 2H); 7.33–7.41 (m, 5H), 7.75 (mc, 2H), 7.94 (mc, 2H). The regiochemistry was determined using NOESY NMR spectroscopy.

Workup

  1. customdried in vacuum
  2. dissolutiondissolved in DCM
  3. washwashed with citric acid

Sources & evidence

ORD record
ord-6873ee8cc2e346fca35bda93506004f7
Source dataset
uspto-grants-2006_06
Patent number
US07064229B2

Reaction notes

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