Lithium Hydroxide → 3-[[2-(4-Methoxyphenyl)acetyl]amino]-2-thiophenecarboxylic acid

HRID 2098159Notes

Reaction equation

HRID 2098159 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:6]>CO>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:13]([NH:12][C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:5]([OH:6])=[O:4])=[O:23])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 897877HCID 897877, compound

Product 1

HCID 201196553-[[2-(4-Methoxyphenyl)acetyl]amino]-2-thiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M lithium hydroxide solution (80 mL) was added to methyl-3-(2-(4-methoxyphenyl)acetamido)thiophene-2-carboxylate (7.30 g, 23.91 mmol) dissolved in methanol. The reaction mixture was refluxed for 2 h, cooled to room temperature and then partitioned between ethyl acetate and H2O. The aqueous layer with acidified with conc HCl, filtered and washed with H2O. The precipitate that formed was collected by filtration (8.55 g, quantitative) and used in the next step without further purification. Method [7] m/z 291.9 (M+H); retention time=3.827. 1H-NMR (CD3OD) δ 8.0 (d, J=5.3 Hz, 1H), 7.61 (d, J=5.3 Hz, 1H), 7.26 (d, J=8.3 Hz, 2H), 6.91 (d, J=8.3 Hz, 2H), 3.76 (s, 3H), 3.70 (s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. custompartitioned between ethyl acetate and H2O
  3. filtrationfiltered
  4. washwashed with H2O
  5. customThe precipitate that formed
  6. filtrationwas collected by filtration (8.55 g, quantitative)
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-f492f337512d4460bd871d6956b6d643
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…