Dicyclohexylcarbodiimide → N-(3-methylthiopropyl)-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704426Notes

Reaction equation

HRID 704426 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]([OH:15])=O)[CH2:11][S:10][CH:9]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23][CH2:24][CH2:25][CH2:26][NH2:27].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:22][S:23][CH2:24][CH2:25][CH2:26][NH:27][C:13]([CH:12]1[CH2:11][S:10][CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 777433-(Methylthio)propylamineHCID 14772789N-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 20074052N-(3-methylthiopropyl)-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamideYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 600 mg of N-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid in 10 ml of tetrahydrofuran, there were added, at 4° C. or below, 200 mg of 3-methylthiopropylamine, 390 mg of 1-hydroxybenzotriazole and 440 mg of dicyclohexylcarbodiimide, in that order, and the mixture was stirred at room temperature for 3 hours. The resultant precipitate was filtered off, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 50 ml or ethyl acetate. The ethyl acetate solution was washed in sequence with 0.5M aqueous citric acid, water, saturated aqueous solution of sodium carbonate and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 250 mg of N-(3-methylthiopropyl)-3-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxamide. Trifluoroacetic acid (2 ml) was added to 250 mg of the thus-obtained compound with ice cooling, and the mixture was treated in the same manner as in Example 4 to give 130 mg of N-(3-methylthiopropyl)-2-(3-pyridyl)thiazolidine-4-carboxamide dihydrochloride as an oil.

Workup

  1. filtrationThe resultant precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 50 ml or ethyl acetate
  4. washThe ethyl acetate solution was washed in sequence with 0.5M aqueous citric acid, water, saturated aqueous solution of sodium carbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f35b9d7c9502484eaa65c4dc176a539f
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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