Lithium Hydroxide → 2-[(4-{3-[Butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid

HRID 899884Notes

Reaction equation

HRID 899884 reaction equation
[CH2:1]([N:5]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[O:37][CH3:38])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[Li+].[OH-].CCOC(C)=O>C1COCC1.O>[CH2:1]([N:5]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[O:37][CH3:38])[C:6](=[O:27])[CH2:7][CH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69120444Methyl 2-[(4-{3-[butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

Product 1

HCID 103914542-[(4-{3-[Butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acidYield 89%

Reagents, catalysts & solvents 1

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

Procedure

Methyl 2-[(4-{3-[butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]-benzoate (15 mg, 0.029 mmol) was dissolved in THF/water (2/1, 2 ml) and LiOH (1.4 mg, 0.058 mmol) was added. The reaction was performed in a single node microwave oven (150° C., 7 min). Workup was done by adding EtOAc (10 ml) and washing the organic phase with two portions of HCl (2×5 ml, 1 M). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 13 mg of 2-[(4-{3-[butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid (yield 89%).

Workup

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

Sources & evidence

ORD record
ord-acad600c2bb64aaebc1da7b66c242a67
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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