Hydrochloric Acid → 4-((2-(Isopropylcarbamoyl)-4-phenoxyphenyl)carbamoyl)benzoic acid

HRID 2099968Notes

Reaction equation

HRID 2099968 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:20][C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=1)=[O:22])=[O:6])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[CH:1]([NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=1)=[O:22])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57796901Methyl 4-((2-(isopropylcarbamoyl)-4-phenoxyphenyl)carbamoyl)benzoate

Product 1

HCID 116616864-((2-(Isopropylcarbamoyl)-4-phenoxyphenyl)carbamoyl)benzoic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 34D (80 mg, 0.19 mmol) in THF (2 mL) was treated with 1 N NaOH (0.4 mL). The resulting solution was stirred for 20 hours. The reaction mixture was treated with 1 N HCl (0.6 mL) and partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and concentrated to afford 34E (75 mg, 94%). HPLC retention time: 4.34 minutes (YMC S-5 ODS-A 4.6×50 mm, 10% to 90% MeOH/H2O w/0.2% H3PO4, 4 minute gradient).

Workup

  1. custompartitioned between EtOAc (20 mL) and water (20 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e540a36ded454a5bb59e6038afaa8650
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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