Water → (3-Chloro-4-{[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid

HRID 1879114Notes

Reaction equation

HRID 1879114 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([O:30]CC)=[O:29])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:14]=[CH:13][C:12]=1[Cl:26])=[O:10].O>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([OH:30])=[O:29])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:14]=[CH:13][C:12]=1[Cl:26])=[O:10]

Participants

5

Reactant 2

HCID 962WaterHCID 59163369Ethyl (3-chloro-4-{[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetate

Product 1

HCID 24952901(3-Chloro-4-{[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acidYield 45.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl (3-chloro-4-{[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetate (72 mg, 0.15 mmol) in acetic acid (3 ml) and 2M HCl (3 ml) was heated at 90° C. for 2 hours. On cooling water was added and the mixture filtered. The resulting solid was dried in vac oven, then triturated with ether to afford the title compound as an off-white solid (32 mg). MS (ES+) m/z 464 [M+H]+ (C24H2035Cl3NO4). 1H-NMR (400 MHz, d6-DMSO) δ 3.63 (2H, s), 5.20 (2H, s), 7.17 (1H, dd, J 8.8, J 2.8), 7.25-7.60 (10H, m), 10.18 (1H, s), 12.5 (1H, s).

Workup

  1. additionwas added
  2. filtrationthe mixture filtered
  3. customThe resulting solid was dried in vac oven
  4. customtriturated with ether

Sources & evidence

ORD record
ord-841a119d1b874577b25be6b2b0f3998d
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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