Lithium Hydroxide → 2-{[2-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid

HRID 898903Notes

Reaction equation

HRID 898903 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]([CH2:31][CH3:32])[C:8](=[O:30])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([O:24]C)=[O:23])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:31][CH3:32])[C:8](=[O:30])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([OH:24])=[O:23])=[CH:13][CH:12]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69258846Methyl 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoate

Product 1

HCID 103230552-{[2-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acidYield 88.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Methyl 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-ethyl]thio}benzoate (0.085 g, 0.170 mmol) was dissolved in a mixture of acetonitrile/water (1/1, 4 ml) and lithium hydroxide (0.008 g, 0.341 mmol) was added. The reaction was performed in an single node microwave oven (5 min. 150 deg). The solvent was removed by evaporation and then HCl (2 ml, 1 M) was added. The water phase was extracted with two portions of EtOAc (20 ml). The combined organic phase was dried (MgSO4) and the solvent was removed by evaporation and gave 0.073 g of 2-{[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid (yield 88.4%) as an oil which solidified on cooling and standing.

Workup

  1. additionwas added
  2. customThe reaction was performed in an single node microwave oven
  3. custom(5 min. 150 deg)
  4. customThe solvent was removed by evaporation
  5. additionHCl (2 ml, 1 M) was added
  6. extractionThe water phase was extracted with two portions of EtOAc (20 ml)
  7. dry with materialThe combined organic phase was dried (MgSO4)
  8. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-3b4216d8d1f64001aa7ae2d34988d7b8
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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