Lithium Hydroxide → HCID 10370253, compound

HRID 899887Notes

Reaction equation

HRID 899887 reaction equation
[CH3:1][O:2][C:3]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:4]=1[CH2:5][N:6]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:7](=[O:28])[CH2:8][CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:12][CH:11]=1.[Li+].[OH-].CCOC(C)=O>C1COCC1.O>[CH3:1][O:2][C:3]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:4]=1[CH2:5][N:6]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:7](=[O:28])[CH2:8][CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69120410HCID 69120410, compound

Product 1

HCID 10370253HCID 10370253, compoundYield 79.4%

Reagents, catalysts & solvents 1

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

Procedure

Methyl 2-[(4-{3-[(2,3-dimethoxybenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]-benzoate (39 mg, 0.069 mmol) was dissolved in THF/water (2/1, 2 ml) and LiOH (3.3 mg, 0.14 mmol) was added. The reaction was performed I a single node microwave oven (150° C., 7 min). Workup was done by adding EtOAc (10 ml) and washing the organic phase with two potions of HCl (2×5 ml, 1 M). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 30 mg of 2-[(4-{3-[(2,3-dimethoxybenzyl)(heptyl)-amino]-3-oxopropyl}phenoxy)methyl]benzoic acid (yield 78.9).

Workup

  1. customI a single node microwave oven (150° C., 7 min)
  2. washwashing the organic phase with two potions of HCl (2×5 ml, 1 M)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-70377a18ef25472085d1e68716fac859
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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