Water → 2-[2-(4-{2-[Ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid

HRID 898893Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 2-[2-(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate (0.200 g, 0.115 mmol) was dissolved in 3 ml THF in a Smith synthesiser vial and then 1.5 ml water and lithium hydroxide (0.032 g, 1.335 mmol) were added to the vial. The vial was capped and put in the microwave oven (Smith synthesiser). The reaction was then heated to 150° C. for 6 minutes. According to LC-MS the reaction was complete. The solvent was evaporated. The residue was dissolved in diethyl ether (30 ml) and washed with NaHCO3 (sat) (2×20 ml). The basic water layer was acidified to pH 1 with 2M HCl. The water layer was extracted with three portions of 20 ml of DCM which were combined, dried and evaporated to give 160 mg of pure desired product.

Workup

customThe vial was capped
customThe solvent was evaporated
dissolutionThe residue was dissolved in diethyl ether (30 ml)
washwashed with NaHCO3 (sat) (2×20 ml)
extractionThe water layer was extracted with three portions of 20 ml of DCM which
customdried
customevaporated

Sources & evidence

ORD record: ord-8bf9a3da95294393af7426c2540205e2
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351858B2

Reaction notes

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