Lithium Hydroxide → 3-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoic acid

HRID 1475689Notes

Reaction equation

HRID 1475689 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:15](NC1(C(O)=O)CCCCCC1)=[O:16].[OH-:33].[Li+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:15]([OH:16])=[O:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 671706151-{3-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoylamino}-cycloheptanecarboxylic acid

Product 1

HCID 671705643-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound of step 1 (530 mg, 1.66 mmol) was dissolved in dioxane (8.3 ml). Lithium hydroxide (8.3 ml of an aqueous 1 M solution) was added and the mixture was kept for 20 min at 60° C. After cooling, the mixture was partitioned between an excess of 2 N hydrochloric acid and EA and the aqueous phase extracted with EA. The combined organic phases were dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was stirred overnight with a mixture of diethyl ether and HEP, filtered, and the solid was dried in vacuo to give 500 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between an excess of 2 N hydrochloric acid and EA
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. filtrationfiltered
  8. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-8298f7495e254d928ba1fb64e6944de6
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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