Sodium Hydroxide → 4-[(1S)-1-({5-Chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid

HRID 493523Notes

Reaction equation

HRID 493523 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[C:6]([CH:22]=1)[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[C:6]([CH:22]=1)[C:7]([NH:9][C@H:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68861972Methyl 4-[(1S)-1-({5-chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoate

Product 1

HCID 116408254-[(1S)-1-({5-Chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[(1S)-1-({5-chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoate (step 6, 407 mg, 1.02 mmol) in methanol (10 ml) was added 2 N sodium hydroxide aqueous solution (2 ml). The reaction mixture was stirred at room temperature for 3 h and then evaporated. The residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic extracts were washed with brine (50 mL), dried (sodium sulfate), and concentrated. The residual solids were recrystallized from ethyl acetate to afford 248 mg (64%) of the title compound as white solids:

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residual solids were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f461730ec1c14fefb955bf69c912863a
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

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