Water → HCID 59314219, compound

HRID 1047732Notes

Reaction equation

HRID 1047732 reaction equation
C([O:3][C:4]([C:6]1([NH:17][C:18]([C:20]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:19])[C@H:14]([CH3:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@@H:7]1[CH3:16])=[O:5])C.[OH-].[K+].O>CCO>[CH3:16][C@H:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:14]([CH3:15])[C:6]1([NH:17][C:18]([C:20]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[CH:23]=[CH:22][CH:21]=1)=[O:19])[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314388HCID 59314388, compound

Product 1

HCID 59314219HCID 59314219, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of (cis)-1,3-dimethyl-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (76) (62 mg, 1.2 mmol) and KOH (300 mg, 5.4 mmol) is dissolved in EtOH (3 mL) and water (0.3 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 pH˜4. The precipitate is filtered to give a pure product (77) as white solid (44 mg, 75%).

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. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-ecd76f8cf9604c299de01d05e5c0bda7
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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