Lithium Hydroxide → HCID 10433857, compound

HRID 898918Notes

Reaction equation

HRID 898918 reaction equation
[CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][S:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25]C)=[O:24])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][S:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([OH:25])=[O:24])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69258703Methyl 2-{[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoate

Product 1

HCID 10433857HCID 10433857, compoundYield 83.5%

Reagents, catalysts & solvents 1

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

Procedure

Methyl 2-{[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoate (0.137 g, 0.296 mmol) was dissolved in a mixture of acetonitrile/water (1/1, 4 ml), lithium hydroxide (0.014 g, 0.591 mmol) was added. The reaction was performed in an single node microwave oven (5 min, 150 deg). Work-up by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The waterphase was extracted with two portions of EtOAc (20 ml), the organic phase was dried (MgSO4) and the solvent was removed by evaporation and gave 0.111 g of 2-{[2-(4-{2[-benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]-thio}benzoic acid (yield 83.5%).

Workup

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

Sources & evidence

ORD record
ord-ffa8ed605ebe4c10aceaab18c116d1b7
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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