Potassium Hydroxide → 2-[(4-{2-[[2-(4-Chlorophenyl)ethyl](heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid

HRID 2112047Notes

Reaction equation

HRID 2112047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:11](=[O:31])[CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:11](=[O:31])[CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68868871Methyl 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate

Product 1

HCID 100754212-[(4-{2-[[2-(4-Chlorophenyl)ethyl](heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acidYield 5.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (0.112 g, 0.209 mmol) was dissolved in EtOH (5 ml, 95%) and potassium hydroxide (0.018 g, 0.313 mmol) was added. The reaction was performed in an single node microwave oven (7 min, 150 deg). Workup was by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The water-phase was extracted with two portions of EtOAc (20 ml) and the organic phase was dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with isocratic 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). The solvent was removed by evaporation to give 0.006 g of 2-[(4-{2-[[2-(4-chlorophenyl)ethyl](heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid (yield 5.5%). 1HNMR (Rotamers, 300 MHz, CDCl3): δ 0.85 (t, 3H), 1.22 (m, 8H), 1.39 (m, 2H), 2.62-3.7 (bm, 8H), 5.45-5.55 (m, 2H), 6.89-7.43 (bm, 9H), 7.52 (m, 1H), 7.78 (t, 1H), 8.13 (t, 1H).

Workup

  1. customThe reaction was performed in an single node microwave oven
  2. custom(7 min, 150 deg)
  3. customby removing the solvent
  4. customby evaporation and addition of HCl (2 ml, 1 M)
  5. extractionThe water-phase was extracted with two portions of EtOAc (20 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation
  8. customThe crude was purified by preparative HPLC (
  9. concentrationthe acetonitrile concentration
  10. temperaturewas increased to 100%
  11. 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)
  12. additionThe product containing fractions
  13. customthe acetonitrile was removed by evaporation EtOAc (10 ml)
  14. additionwas added
  15. washthe organic phase was washed with two portions of brine
  16. dry with materialdried (MgSO4)
  17. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2ec00eafca0246d69ec76466882fb758
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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