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Hydrochloric Acid → 2-{[4-(3-{[2-(2-Ethoxyphenyl)ethyl]amino}-3-oxopropyl)phenoxy]methyl}benzoic acid

HRID 2112031
Notes
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Reaction equation

HRID 2112031 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][C:13](=[O:34])[CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26]C)=[O:25])=[CH:18][CH:17]=1)[CH3:2].[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][NH:12][C:13](=[O:34])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([OH:26])=[O:25])=[CH:32][CH:33]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68870250Methyl 2-{[4-(3-{[2-(2-ethoxyphenyl)ethyl]amino}-3-oxopropyl)phenoxy]methyl}benzoate

Product 1

HCID 100492792-{[4-(3-{[2-(2-Ethoxyphenyl)ethyl]amino}-3-oxopropyl)phenoxy]methyl}benzoic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 21881883
Oxolane--water (1/1)
Solvent

Procedure

Methyl 2-{[4-(3-{[2-(2-ethoxyphenyl)ethyl]amino}-3-oxopropyl)phenoxy]methyl}-benzoate (0.26 g, 0.56 mmol) was dissolved in a mixture of THF/water (7/1, 5 ml) and lithium hydroxide (54 mg, 2.25 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). The reaction mixture was acidified (HCl, 1 M, 1 ml) and the water phase was washed with two portions of EtOAc (2×5 ml). The organic phases were combined, dried (MgSO4) and the solvent was removed by evaporation. The crude product was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). Removing the solvent by evaporation gave 136 mg of 2-{[4-(3-{[2-(2-ethoxyphenyl)ethyl]amino}-3-oxopropyl)phenoxy]methyl}benzoic acid (yield 53.9%).

Workup

  1. additionwas added
  2. customThe reaction was performed in a single node microwave oven
  3. custom(7 min, 150° C.)
  4. washthe water phase was washed with two portions of EtOAc (2×5 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe crude product was purified by preparative HPLC (
  8. concentrationthe acetonitrile concentration
  9. temperaturewas increased to 100%
  10. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min))
  11. additionThe product containing fractions
  12. customthe acetonitrile was removed by evaporation
  13. additionEtOAc (10 ml) was added
  14. washthe organic phase was washed with two portions of brine
  15. dry with materialdried (MgSO4)
  16. customRemoving the solvent
  17. customby evaporation

Sources & evidence

ORD record
ord-e08ba855c87e476484e28360c58e0f6c
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07521461B2

Reaction notes

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