Hydrochloric Acid → [4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid

HRID 2373714Notes

Reaction equation

HRID 2373714 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28]([O:30]C)=[O:29])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1.[OH-].[Na+].Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28]([OH:30])=[O:29])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86607183Methyl [4-(2-chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate

Product 1

HCID 69200552[4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl [4-(2-chlorophenyl)-2-(4-{[( 1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate (0.145 g, 0.328 mmol) was dissolved in EtOH (2 mL). NaOH (0.65 mL, 1N, 0.65 mmol) was added and the solution heated to reflux for 5 h. HCl (0.35 mL, 2N, 0.70 mmol) was added and the solvent removed. The mixture was partitioned between EtOAc and H2O. The EtOAc layer was dried (MgSO4) and the solvent removed to yield [4-(2-chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid (0.138 g) as a white solid. mp 101-103° C. 1H NMR (500 MHz, DMSO-d6) δ: 0.88 (t, 6H, J=7.3 Hz), 1.50 (m, 2H), 1.55 (m, 2H), 3.42 (s, 2H), 3.82 (m, 1H), 7.35 (m, 1H), 7.42 (m, 3H), 7.58 (m, 3H), 7.96 (d, 2H, J=8.4 Hz), 8.11 (d, 1H, J=8.7 Hz). MS (ES) m/z 442.1 ([M+H]+). MS (ES) m/z 883.1 ([2M+H]+). Anal. Calcd for C24H24ClNO3S: C, 65.22; H, 5.47; N, 3.17. Found: C, 62.33; H, 5.54; N, 3.01.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 5 h
  3. customthe solvent removed
  4. customThe mixture was partitioned between EtOAc and H2O
  5. dry with materialThe EtOAc layer was dried (MgSO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-391e51f0da5f4e2a8ed15adf550e0229
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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