Sodium Hydroxide → HCID 67078571, compound

HRID 2360086Notes

Reaction equation

HRID 2360086 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[C:20]([NH:22][CH2:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)=[O:21])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C.COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:11][C:10]=2[C:20]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=2)=[O:21])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67078680HCID 67078680, compound

Product 1

HCID 67078571HCID 67078571, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoate (1.5 g, 3.41 mmol) dissolved in ethanol (85 ml) and ethyleneglycol dimethyl ether (3.41 ml), 10% NaOH (34.1 ml, aqueous solution) was added dropwise. The resulting mixture was stirred under reflux and the progress of the reaction was monitored by TLC. Upon completion of the reaction, ethanol was removed under reduced pressure and the resulting aqueous solution was cooled to 0° C., neutralized with HCl 6N and extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure, to obtain 1.26 g of 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoic acid: Yield 88%; m.p. 260° C. (dec); IR 3408, 3268, 1684, 1525, 1496, 1264 cm−1; 1H-NMR (300 MHz, δ ppm, DMSO-d6) 11.57 (s, 1H), 8.00 (t, J=5.9 Hz, 1H), 7.90 (d, J=8.2 Hz, 2H), 7.80 (d, J=7.3 Hz, 2H), 7.46-7.35 (m, 7H), 7.27 (d, J=7.0 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 6.67 (d, J=2.2 Hz, 1H), 4.47 (d, J=5.5 Hz, 2H), 3.76 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 167.1, 160.9, 157.9, 144.8, 133.0, 131.5, 130.1, 129.2, 128.8, 128.5, 128.0, 127.3, 126.7, 124.6, 122.3, 113.1, 108.5, 55.0, 42.0.

Workup

  1. temperatureunder reflux
  2. customwas removed under reduced pressure
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-949f8de92f1646febbf23895a59c6071
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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