Triethylamine → HCID 13145506, compound

HRID 850950Notes

Reaction equation

HRID 850950 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.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:33][C:34]1[S:35][CH:36]=[N:37][N:38]=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]([NH:33][C:34]1[S:35][CH:36]=[N:37][N:38]=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

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 199091,3,4-Thiadiazol-2-amineHCID 2466732-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid

Product 1

HCID 13145506HCID 13145506, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9.6 g of N-benzyloxycarbonyl-DL-leucine and 3.7 g of triethylamine were dissolved in 150 ml of chloroform, to which was added dropwise 3.9 g of ethyl chlorocarbonate under sodium chloride-ice cooling conditions. The solution was stirred for 2 hours, to which was then added 3.7 g of 2-amino-1,3,4-thiadiazole, followed by stirring for further 24 hours. The reaction solution was washed with water, and after drying, the solvent was removed by distillation to obtain 9.0 g (yield: 71%) of 2-(N-benzyloxycarbonyl-DL-leucylamino)-1,3,4-thiadiazole as white crystals having a melting point of 118°-120° C.

Workup

  1. stirringby stirring for further 24 hours
  2. washThe reaction solution was washed with water
  3. customafter drying
  4. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-ecd81b84f7fc4cf99eeaf1635f861a37
Source dataset
uspto-grants-1983_05
Patent number
US04382142

Reaction notes

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