Thiazolidine → HCID 131716923, compound

HRID 1086275Notes

Reaction equation

HRID 1086275 reaction equation
[CH:1]1([CH2:10][C:11]([CH:13]2[S:17][CH2:16][NH:15][C@@H:14]2[C:18]([OH:20])=O)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.[S:33]1[CH2:37][CH2:36][NH:35][CH2:34]1>C(Cl)Cl>[CH:1]1([CH2:10][C:11]([CH:13]2[S:17][CH2:16][NH:15][C@@H:14]2[C:18]([N:35]2[CH2:36][CH2:37][S:33][CH2:34]2)=[O:20])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10444ThiazolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1317169183-(2-indanylacetyl)-L-thioproline

Product 1

HCID 131716923HCID 131716923, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.60 g .COPYRGT.f 3-(2-indanylacetyl)-L-thioproline was suspended in 5 ml of methylene chloride. To the suspension was added 0.46 g of WSC HCl with stirring at room temperature. After 5 minutes, 0.18 g of thiazolidine dissolved in 5 ml of methylene chloride was added to the mixture, and the mixture was stirred for 17 hours at room temperature. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to produce 0.40 g of 3-[3-(2-indanylacetyl)-L-thioprolyl]thiazolidine as a colorless oil (yield: 55%).

Workup

  1. additionwas added to the mixture
  2. stirringthe mixture was stirred for 17 hours at room temperature
  3. washThe reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddb8d23431a3472d85ab6ce017c36888
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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