Benzyl Bromide → HCID 86646468, compound

HRID 1811448Notes

Reaction equation

HRID 1811448 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])[CH:20]=[CH:21][C:22]=2[OH:24])[CH2:17][CH2:16][C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.S([O-])(O)(=O)=O.[K+]>O.CS(C)=O>[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])[CH:20]=[CH:21][C:22]=2[O:24][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:17][CH2:16][C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 516920Potassium bisulfateHCID 23665647Potassium tert-butoxideHCID 86613946HCID 86613946, compound

Product 1

HCID 86646468HCID 86646468, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

55.5 mg of potassium tert-butoxide was added to a DMSO solution (1 ml) of 90 mg of 5-(1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione, followed by stirring at room temperature for 1 hour. 30 μl of benzyl bromide was added thereto, followed by stirring at room temperature for 1 hour. Water was added to the reaction liquid, potassium hydrogensulfate was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by preparative silica gel thin layer chromatography (dichloromethane:methanol=20:1), giving 84.5 mg (76% yield) of 5-(1-benzyl-8-benzyloxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as a colorless amorphous solid.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative silica gel thin layer chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-e5a07db3e369435a91d7fed6208d67e3
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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