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

HRID 1966955Notes

Reaction equation

HRID 1966955 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:29])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]3([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:20](=[O:27])[NH:19][C:18]2=[O:28])=[CH:13][CH:12]=1)[CH3:8].Cl[CH2:31][C:32]([NH:34][C:35]1[C:40]([CH:41]([CH3:43])[CH3:42])=[CH:39][CH:38]=[CH:37][C:36]=1[CH:44]([CH3:46])[CH3:45])=[O:33].O>CN(C)C=O>[CH2:7]([O:9][C:10](=[O:29])[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:21]3([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:20](=[O:27])[N:19]([CH2:31][C:32](=[O:33])[NH:34][C:35]3[C:36]([CH:44]([CH3:46])[CH3:45])=[CH:37][CH:38]=[CH:39][C:40]=3[CH:41]([CH3:43])[CH3:42])[C:18]2=[O:28])=[CH:15][CH:16]=1)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamideHCID 666812434-(2,4-Dioxo-1,3-diazaspiro[4.5]dec-1-yl)benzoic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

87 mg (0.63 mmol, 1 eq.) of potassium carbonate are added to a solution of 200 mg (0.63 mmol, 1 eq.) of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-1-yl)benzoic acid ethyl ester and 160 mg (0.63 mmol, 1 eq.) of 2-chloro-N-(2,6-diisopropylphenyl)acetamide in 30 ml of dimethylformamide. The reaction medium is stirred at room temperature overnight. It is then poured into water and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off. The residue is precipitated from dichloromethane and heptane. The product 4-{3-[(2,6-diisopropyl-phenylcarbamoyl)methyl]-2,4-dioxo-1,3-diaza-spiro[4.5]dec-1-yl}benzoic acid ethyl ester is obtained in the form of a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThey are dried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customThe residue is precipitated from dichloromethane and heptane

Sources & evidence

ORD record
ord-93076453713a4a379dbb906704e00326
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

Loading…