Dimethylformamide → HCID 86613962, compound

HRID 504051Notes

Reaction equation

HRID 504051 reaction equation
CN(C=O)C.[OH:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[C:15]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:11]1=[O:28].C(=O)([O-])[O-].[K+].[K+].[C:35]1([C:41](Cl)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[OH:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[C:15]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[N:23]([C:41]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:22]3=[O:27])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:11]1=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 86613963HCID 86613963, compound

Product 1

HCID 86613962HCID 86613962, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF solution (10 ml) of 1.0 g (2.99 mmol) of 5-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione and 0.455 g (3.29 mmol) of potassium carbonate was cooled with ice, and 0.876 g (3.04 mmol) of triphenylmethylchloride was added thereto, followed by stirring at room temperature overnight. Water was added to the reaction liquid and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water and once with saturated sodium chloride solution, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→ethyl acetate). The purified product was concentrated under reduced pressure and evaporated to dryness, giving 700 mg (40.6% yield) of 5-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]-3-tritylthiazolidine-2,4-dione as a colorless amorphous solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed twice with water and once with saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→ethyl acetate)
  6. concentrationThe purified product was concentrated under reduced pressure
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-bb1216aab0eb4102810d8e97d461a245
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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