Water → HCID 25159483, compound

HRID 1047739Notes

Reaction equation

HRID 1047739 reaction equation
C([O:3][C:4]([C:6]1([NH:19][C:20]([C:22]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[O:21])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[C:22]1([C:20]([NH:19][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=3)[CH2:7]2)=[O:21])[C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68589873HCID 68589873, compound

Product 1

HCID 25159483HCID 25159483, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-5-trifluoromethyl-indan-2-carboxylic acid ethyl ester (84) (437 mg, 1.0 mmol) and KOH (1 g, 18 mmol) is dissolved in EtOH (8 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 3 h. After concentration in vacuo, the residue is dissolved in water (50 mL) and acidified with conc. HCl until no more white precipitate formed. The precipitate is filtered to give a pure product (85) as white solid (408 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 (50 mL)
  6. customformed
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-b93c4e28641b4aa1989141c43e8f3f4e
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…