4-{3-[(2,6-Diisopropylphenylcarbamoyl)-methyl]-2,4-dioxo-1,3-diazaspiro[4.5]dec-1-yl}benzoic acid ethyl ester → 4-{3-[(2,6-Diisopropylphenylcarbamoyl)methyl]-2,4-dioxo-1,3-diaza-spiro[4.5]dec-1-yl}benzoic acid methyl ester

HRID 1966961Notes

Reaction equation

HRID 1966961 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:14](=[O:21])[N:13]([CH2:22][C:23](=[O:37])[NH:24][C:25]3[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=3[CH:34]([CH3:36])[CH3:35])[C:12]2=[O:38])=[CH:7][CH:6]=1)C>CO.S(=O)(=O)(O)O>[CH3:1][O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:14](=[O:21])[N:13]([CH2:22][C:23](=[O:37])[NH:24][C:25]3[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=3[CH:34]([CH3:35])[CH3:36])[C:12]2=[O:38])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 468924814-{3-[(2,6-Diisopropylphenylcarbamoyl)-methyl]-2,4-dioxo-1,3-diazaspiro[4.5]dec-1-yl}benzoic acid ethyl ester

Product 1

HCID 468926114-{3-[(2,6-Diisopropylphenylcarbamoyl)methyl]-2,4-dioxo-1,3-diaza-spiro[4.5]dec-1-yl}benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

33 mg of 4-{3-[(2,6-diisopropylphenylcarbamoyl)-methyl]-2,4-dioxo-1,3-diazaspiro[4.5]dec-1-yl}benzoic acid ethyl ester are dissolved in 10 ml of methanol, 1 drop of concentrated sulfuric acid is added and the solution is refluxed for 18 hours. The mixture is stirred at reflux for 72 hours. The solvent is evaporated off. The residue is dissolved in DCM, heptane is added until slight cloudiness appears, and the solution is stirred at room temperature under nitrogen for 16 hours. The product 4-{3-[(2,6-diisopropylphenylcarbamoyl)methyl]-2,4-dioxo-1,3-diaza-spiro[4.5]dec-1-yl}benzoic acid methyl ester is obtained in the form of fine white needles.

Workup

  1. temperaturethe solution is refluxed for 18 hours
  2. temperatureat reflux for 72 hours
  3. customThe solvent is evaporated off
  4. dissolutionThe residue is dissolved in DCM
  5. additionheptane is added until slight cloudiness
  6. stirringthe solution is stirred at room temperature under nitrogen for 16 hours

Sources & evidence

ORD record
ord-a3b9813574ba410891fc0da9dbd1bd25
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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