Hydrochloric Acid → 4-[(1S)-1-({[5-Chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid

HRID 1293241Notes

Reaction equation

HRID 1293241 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]([NH:19][C@H:20]([C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=2)[CH3:21])=[O:18])[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[CH3:16])=[N:6][CH:7]=1.[OH-].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]([NH:19][C@H:20]([C:22]2[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=2)[CH3:21])=[O:18])[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[CH3:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69418363methyl 4-[(1S)-1-({[5-chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

Product 1

HCID 116694614-[(1S)-1-({[5-Chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-[(1S)-1-({[5-chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate (step 2, 230 mg, 0.56 mmol), N,N-dimethylformamide (5 mL), and 2 M sodium hydroxide aqueous solution (2.5 mL) was stirred at room temperature for 16 h. The mixture was poured into 2 M hydrochloric acid (30 mL), and extracted with ethyl acetate (100 mL×2). The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flush column chromatography on silica gel eluting with dichloromethane/methanol (20/1) to give 191 mg (86%) of the title compound as white solids: 1H-NMR (DMSO-d6) δ 9.06 (1H, d, J=7.9 Hz), 8.25 (1H, d, J=2.6 Hz), 8.15 (1H, d, J=2.6 Hz), 7.88 (2H, d, J=8.1 Hz), 7.53 (2H, d, J=8.2 Hz), 7.46–7.15 (1H, m), 5.24–5.14 (1H, m), 2.10 (3H, s), 1.47 (3H, d, J=6.9 Hz); MS (ESI) m/z 445 (M+H)+, 443 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate (100 mL×2)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified
  5. customby flush column chromatography on silica gel eluting with dichloromethane/methanol (20/1)

Sources & evidence

ORD record
ord-bb9cef581acb400cbd3bdd0b144b5730
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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