4-Methylmorpholine → HCID 14881632, compound

HRID 704431Notes

Reaction equation

HRID 704431 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]2[NH:26][CH:25]([C:27]([OH:29])=O)[CH2:24][S:23]2)[CH:17]=1.[CH2:30]([O:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>O1CCCC1.C(OCC)(=O)C>[CH2:30]([O:37][NH:38][C:27]([CH:25]1[CH2:24][S:23][CH:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[NH:26]1)=[O:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 102313O-BenzylhydroxylamineHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 14881632HCID 14881632, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 490 mg of dicyclohexylcarbodiimide in 5 ml of tetrahydrofuran was added dropwise to a mixture of 500 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, mg of O-benzylhydroxylamine, 480 mg of 1-hydroxybenzotriazole, 240 mg of N-methylmorpholine and 15 ml of tetrahydrofuran with ice cooling, and the resultant mixture was stirred with ice cooling for 1 hour and then at room temperature for 12 hours. The reaction mixture was diluted with 30 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (eluent:ethyl acetate) gave 260 mg of N-benzyloxy-2-(3-pyridyl)thiazolidine-4-carboxamide. This compound was dissolved in ethyl acetate, and 1.5 ml of 2N hydrogen chloride solution in dioxane was added. The resultant solid was collected by filtration, washed with ethyl acetate and dried to give 240 mg of N-benzyloxy-2-(pyridin-3-yl)thiazolidine-4-carboxamide dihydrochloride. Melting point 115° C.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by silica gel column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-ccfa3a0daf4e4e4eaace8a3a2a1b2f04
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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