Lithium hydroxide, monohydrate → 2-[3-(4-Fluoro-benzylamino)-4-methoxy-benzoylamino]-indane-2-carboxylic acid

HRID 521472Notes

Reaction equation

HRID 521472 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]([O:22][CH3:23])=[C:18]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=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].O.[OH-].[Li+]>CO.O>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[O:22][CH3:23])[C:15]([NH:14][C:5]2([C:3]([OH:4])=[O:2])[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13]2)=[O:33])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 670768002-[3-(4-Fluoro-benzylamino)-4-methoxy-benzoylamino]-indane-2-carboxylic acid methyl ester

Product 1

HCID 670766192-[3-(4-Fluoro-benzylamino)-4-methoxy-benzoylamino]-indane-2-carboxylic acidYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound of step 1 (30 mg, 0.053 mmol) was dissolved in methanol (3 ml) and water (1 ml). Lithium hydroxide hydrate (3.8 mg, 0.09 mmol) was added, and the mixture was stirred at room temperature until LC/MS analysis showed complete conversion. The mixture was filtered, the filtrate subjected to preparative RP HPLC (water/ACN gradient), and the fractions containing the title compound freeze-dried to give 19 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe fractions containing the title compound
  3. customfreeze-dried

Sources & evidence

ORD record
ord-fe9aaf772dad40b9b269cb7ce80778f6
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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