Lithium Hydroxide → 2-[(4-{3-[(3-Ethoxypropyl)(4-isopropylbenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid

HRID 899891Notes

Reaction equation

HRID 899891 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=1)[C:8](=[O:29])[CH2:9][CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=1)[CH3:2].[Li+].[OH-].CCOC(C)=O>C1COCC1.O>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:38])[CH3:39])=[CH:33][CH:32]=1)[C:8](=[O:29])[CH2:9][CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69134058Methyl 2-[(4-{3-[(3-ethoxypropyl)(4-isopropylbenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

Product 1

HCID 162235212-[(4-{3-[(3-Ethoxypropyl)(4-isopropylbenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acidYield 69.5%

Reagents, catalysts & solvents 1

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

Procedure

Methyl 2-[(4-{3-[(3-ethoxypropyl)(4-isopropylbenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate (0.16 g, 0.30 mmol) was dissolved in THF/water (2/1, 2 ml) and LiOH (14.4 mg, 0.60 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 0.108 gram of 2-[(4-{3-[(3-ethoxypropyl)(4-isopropylbenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid (yield 69.3%).

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-d41dbd621cd6428da1c20fb8283733fc
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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