Triethylamine → 2-(t-butoxycarbonyl-DL-threonyl)amino-1,3,4-thiadiazole

HRID 1156408Notes

Reaction equation

HRID 1156408 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:29][C:30]1[S:31][CH:32]=[N:33][N:34]=1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([NH:29][C:30]1[S:31][CH:32]=[N:33][N:34]=1)=[O:15])[CH:10]([CH3:12])[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 199091,3,4-Thiadiazol-2-amineHCID 100116N-(tert-butyloxycarbonyl)-L-threonine

Product 1

HCID 130379942-(t-butoxycarbonyl-DL-threonyl)amino-1,3,4-thiadiazoleYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved in tetrahyrofuran were 6.6 g of t-butyoxycarbonyl-DL-threonine and 3.1 g of triethylamine, to which was added dropwise 3.3 g of ethyl chlorocarbonate at 0° C. After stirring for two hours, 3.1 g of 2-amino-1,3,4-thiadiazole was added, and stirred at room temperature for further 20 hours. The reaction solution was concentrated under a reduced pressure, water was added to the residue, and the precipitates were collected by filtration to obtain 7.2 g (Yield 80%) of 2-(t-butoxycarbonyl-DL-threonyl)amino-1,3,4-thiadiazole as white crystals having a melting point of from 165° to 172° C. (dec.).

Workup

  1. stirringstirred at room temperature for further 20 hours
  2. concentrationThe reaction solution was concentrated under a reduced pressure, water
  3. additionwas added to the residue
  4. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-e50e1f8da1fc4cedbd451fa61782d191
Source dataset
uspto-grants-1982_06
Patent number
US04335247

Reaction notes

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