Cyanogen Bromide → HCID 86701010, compound

HRID 1855170Notes

Reaction equation

HRID 1855170 reaction equation
C([O-])(O)=O.[Na+].OC(C(F)(F)F)=O.[CH2:13]([O:20][N:21]1[C:27](=[O:28])[N:26]2[CH2:29][C@H:22]1[CH2:23][CH2:24][C@H:25]2[C:30]([NH:32][NH2:33])=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N:34]#[C:35]Br>O1CCOCC1>[NH2:34][C:35]1[O:31][C:30]([C@@H:25]2[CH2:24][CH2:23][C@@H:22]3[CH2:29][N:26]2[C:27](=[O:28])[N:21]3[O:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:32][N:33]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 131732350HCID 131732350, compound

Product 1

HCID 86701010HCID 86701010, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Saturated NaHCO3 (7.0 mL, 6.26 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide TFA salt (2.3 g, 5.69 mmol) in dioxane (11.4 mL) and the reaction mixture was stirred at rt for 5 minutes. Cyanic bromide (3 M solution, 2.3 mL, 6.90 mmol) was added and the reaction mixture was stirred at rt for 30 minutes. The reaction mixture was then loaded on a silica gel cartridge and purified by silica gel column chromatography (gradient elution 0-10% MeOH/DCM) to give (2S,5R)-2-(5-amino-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one (0.57 g, 32%). ESI-MS (EI+, m/z): 316.4 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at rt for 30 minutes
  2. custompurified by silica gel column chromatography (gradient elution 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-28c1324e0ca746b096471961f320485e
Source dataset
uspto-grants-2015_02
Patent number
US08962843B2

Reaction notes

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