Water → 2-[2,4-Dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

HRID 1771684Notes

Reaction equation

[Cl:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[CH:19][C:18]=2[F:30])=[C:13]([Cl:31])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].O[Li].O.O>C1COCC1>[Cl:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[CH:20]=[CH:19][C:18]=2[F:30])=[C:13]([Cl:31])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-[2,4-dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (130 mg, 0.28 mmol, 1.0 eq) in THF (20 mL), LiOH.H2O (50 mg, 1.1 mmol, 4.0 eq) was added. After the addition of water (10 mL), the mixture was heated to 60° C. overnight. The THF was then removed in vacuo and the water phase was adjusted to pH 6 by addition of 1M HCl. The precipitate was collected by filtration, washed with water and dried in vacuo to give the title compound as a solid (80 mg, 65%).

Workup

customThe THF was then removed in vacuo
additionthe water phase was adjusted to pH 6 by addition of 1M HCl
filtrationThe precipitate was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-a5c51c34b9ac4a148af53a31620e5225
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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