Water → HCID 59314279, compound

HRID 1047721Notes

Reaction equation

HRID 1047721 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:27]3[CH2:26][CH2:25][CH2:24][C:23](=[O:28])[C:22]=3[CH:21]=[CH:20][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>[O:28]=[C:23]1[CH2:24][CH2:25][CH2:26][C:27]2[C:18]([C:16]([NH:15][C:6]3([C:4]([OH:5])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[O:17])=[CH:19][CH:20]=[CH:21][C:22]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314387HCID 59314387, compound

Product 1

HCID 59314279HCID 59314279, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(5-oxo-5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (65) (250 mg, 0.66 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (10 mL) and water (0.5 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 (20 mL) and acidified with conc. HCl until no more white precipitate formed. After the filtration, the solid is purified by HPLC to give a pure product (66) as white solid (150 mg, 65%).

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 (20 mL)
  6. customformed
  7. filtrationAfter the filtration
  8. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-0c611d574c144b1ea2408613c3450715
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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