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

HRID 2094659Notes

Reaction equation

HRID 2094659 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-cac0f31f197542d1a23f08ee3560cd1a
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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