Thiazolidine → N-(4-phenyl-butanoyl)-L-thioprolylthiazolidine

HRID 850365Notes

Reaction equation

HRID 850365 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:12]2[CH2:19][S:18][CH2:17][C@H:13]2[C:14]([OH:16])=O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:12]2[CH2:19][S:18][CH2:17][C@H:13]2[C:14]([CH:21]2[NH:22][CH2:23][CH2:24][S:20]2)=[O:16])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10444ThiazolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14672237N-(4-phenylbutanoyl)-L-thioproline

Product 1

HCID 131721612N-(4-phenyl-butanoyl)-L-thioprolylthiazolidineYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 20 ml of methylene chloride, 1.4 g of the thus-obtained N-(4-phenylbutanoyl)-L-thioproline were added together with 445 mg of thiazolidine and 1.05 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [WSC (Water Soluble Carbodiimide).HCl], and the mixture was stirred for 24 hours. The resultant liquid reaction mixture was washed with 1N hydrochloric acid, saturated saline, a saturated aqueous solution of sodium bicarbonate and saturated saline in that order and dried over anhydrous sodium sulfate. Methylene chloride was distilled off, and the resultant oily residue was subjected to column chromatography on silica gel, thereby obtaining 833 mg of the intended N-(4-phenyl-butanoyl)-L-thioprolylthiazolidine as colorless crystals from a chloroform-methanol fraction.

Workup

  1. customThe resultant liquid reaction mixture
  2. washwas washed with 1N hydrochloric acid, saturated saline
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated saline in that order and dried over anhydrous sodium sulfate
  4. distillationMethylene chloride was distilled off

Sources & evidence

ORD record
ord-cd8750474a1c4ac49c88293455c455c7
Source dataset
uspto-grants-2000_01
Patent number
US06017929

Reaction notes

Loading…