Lithium Hydroxide → 2-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

HRID 521432Notes

Reaction equation

HRID 521432 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[C:18]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[OH-].[Li+]>O1CCOCC1>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:5]2([C:3]([OH:4])=[O:2])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:33])=[CH:17][C:18]=1[O:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 670764352-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

Product 1

HCID 670766762-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acidYield 73.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound of example 1 (60 mg, 0.118 mmol) was dissolved in dioxane (1.5 ml), lithium hydroxide (0.59 ml of an aqueous 1 M solution) was added and the mixture was reacted for 20 min at 60° C. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the organic extracts 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 43 mg of the title compound.

Workup

  1. customthe mixture was reacted for 20 min at 60° C
  2. customThe mixture was partitioned between 2 N hydrochloric acid and EA
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialthe organic extracts 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-b703b1398d2544d1a3eea50f4a856dac
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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