Dicyclohexylcarbodiimide → HCID 13145506, compound

HRID 850952Notes

Reaction equation

HRID 850952 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[S:22][CH:23]=[N:24][N:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]([NH:20][C:21]1[S:22][CH:23]=[N:24][N:25]=1)=[O:19])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 199091,3,4-Thiadiazol-2-amineHCID 2466732-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid

Product 1

HCID 13145506HCID 13145506, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

26.5 g of N-benzyloxycarbonyl-DL-leucine and 10 g of 2-amino-1,3,4-thiadiazole were dissolved in 80 ml of dioxane, to which was added dropwise 20 ml of a dioxane solution of 20.6 g of N,N'-dicyclohexylcarbodiimide, followed by stirring at room temperature for 24 hours. The solvent was removed from the reaction solution by distillation under reduced pressure, and the residue was recrystallized from diluted ethanol to obtain 20.9 g (yield: 56%) of 2-(N-benzyloxycarbonyl-DL-leucylamino)-1,3,4-thiadiazole as colorless crystals having a melting point of 121° C. (dec.).

Workup

  1. customThe solvent was removed from the reaction solution by distillation under reduced pressure
  2. customthe residue was recrystallized from diluted ethanol

Sources & evidence

ORD record
ord-eda5dbb8077e4bd7b31cafddbb9606db
Source dataset
uspto-grants-1983_05
Patent number
US04382142

Reaction notes

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