Water → HCID 59314304, compound

HRID 1047723Notes

Reaction equation

HRID 1047723 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]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>[C@H:18]1([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:17])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314141HCID 59314141, compound

Product 1

HCID 59314304HCID 59314304, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[((R)-1,2,3,4-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (67) (440 mg, 1.21 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 3 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. The precipitate is filtered to give a pure product (68) as white solid (391 mg, 96%).

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. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-fa5386b371934906a104451414bef0d8
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…