Lawesson's reagent → HCID 86701403, compound

HRID 870859Notes

Reaction equation

HRID 870859 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:20][NH:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)=[S:23])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>C1COCC1.[Hg](OC(C)=O)OC(C)=O>[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[S:23][C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[N:21][N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 86701402HCID 86701402, compound

Product 1

HCID 86701403HCID 86701403, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo [3.2.1]octane-2-carbonyl)hydrazinecarbonothioyl)piperazine-1-carboxylate (0.66 g, 1.27 mmol) and Lawesson's reagent (0.36 g, 0.89 mmol) in THF (15 mL) was heated at 66° C. for 1 h, then cooled down to rt Hg(OAc)2 (0.4 g) was added and the mixture was stirred at rt overnight. The solution was then concentrated and the residue was purified by silica gel column chromatography (1:2 EtOAc/petroleum ether) to give tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-thiadiazol-2-yl)piperazine-1-carboxylate (0.15 g, 24%) as a light yellow solid. ESI-MS (EI+, m/z): 501 [M+H]+.

Workup

  1. additionwas added
  2. concentrationThe solution was then concentrated
  3. customthe residue was purified by silica gel column chromatography (1:2 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-8f762226f67a47dcabb4c2324dbd17d9
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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