Water → 2-[(6-Fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acid

HRID 1047717Notes

Reaction equation

HRID 1047717 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:27]3[O:26][CH2:25][O:24][CH2:23][C:22]=3[CH:21]=[C:20]([F:28])[CH:19]=2)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[F:28][C:20]1[CH:19]=[C:18]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14]2)=[O:17])[C:27]2[O:26][CH2:25][O:24][CH2:23][C:22]=2[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593143692-[(6-Fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143802-[(6-Fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(6-fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (61) (560 mg, 1.45 mmol) and KOH (1 g, 17.9 mmol) is dissolved in EtOH (10 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl until no more precipitate came out of the water. After the filtration, the solid is purified by HPLC to give a pure product (62) as white solid (520 mg, 100%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (30 mL)
  6. filtrationAfter the filtration
  7. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-49f2782601a541cf812d584035083f48
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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