Triethylamine → HCID 54117209, compound

HRID 1722661Notes

Reaction equation

HRID 1722661 reaction equation
Cl.[S:2]1[CH2:6][C@@H:5]([C:7]([N:9]2[CH2:13][CH2:12][S:11][CH2:10]2)=[O:8])[NH:4][CH2:3]1.Cl.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:15]([N:4]1[C@H:5]([C:7]([N:9]2[CH2:13][CH2:12][S:11][CH2:10]2)=[O:8])[CH2:6][S:2][CH2:3]1)(=[O:22])[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 70384933HCID 70384933, compound

Product 1

HCID 54117209HCID 54117209, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.48 g of 3-[(R)-(-)-thiazolidine-4-carbonyl]thiazolidine hydrochloride and 0.36 g of isonicotinoylchloride hydrochloride in 10 ml of dichloromethane was added 1.6 ml of triethylamine with stirring under cooling. The reaction mixture was stirred for 24 hours at room temperature, and then washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/acetonitrile=1/1) to obtain 0.46 g of 3-[(R)-(-)-3-isonicotinoylthiazolidine-4-carbonyl]thiazolidine (yield: 42%).

Workup

  1. temperatureunder cooling
  2. stirringThe reaction mixture was stirred for 24 hours at room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/acetonitrile=1/1)

Sources & evidence

ORD record
ord-ef6d115435cf48ccab7580f29efc2004
Source dataset
uspto-grants-1989_08
Patent number
US04857524

Reaction notes

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