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

HRID 1810872Notes

Reaction equation

HRID 1810872 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-2bc46534770f44c5812778f9519495b7
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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