Pyridine → HCID 86701381, compound

HRID 515605Notes

Reaction equation

HRID 515605 reaction equation
O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[C:16]([NH:19][NH:20][C:21]([C@@H:23]1[CH2:29][CH2:28][C@@H:27]2[CH2:30][N:24]1[C:25](=[O:39])[N:26]2[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:22])(=O)[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:32]([O:31][N:26]1[C:25](=[O:39])[N:24]2[CH2:30][C@H:27]1[CH2:28][CH2:29][C@H:23]2[C:21]1[O:22][C:16]([CH3:17])=[N:19][N:20]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86694021HCID 86694021, compound

Product 1

HCID 86701381HCID 86701381, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(CF3SO2)2O (0.50 mL) was slowly added to a solution of (2S,5R)—N′-acetyl-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (0.5 g) and pyridine (0.5 mL) in dry DCM (10 mL) at −10° C. The reaction mixture was stirred at 0° C. for 1 h and then quenched carefully with sat. NaHCO3. The organic layer was separated and the aqueous layer was exacted with EtOAc (3×). The combined organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography (gradient elution 10:1 to 1:1 petroleum ether/EtOAc) to afford (2S,5R)-6-(benzyloxy)-2-(5-methyl-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (0.3 g, 63%) as a slight yellow solid. ESI-MS (EI+, m/z): 315.0 [M+H]+.

Workup

  1. customquenched carefully with sat. NaHCO3
  2. customThe organic layer was separated
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (gradient elution 10:1 to 1:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-3ff0909da9364f549997d0552cd11713
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

Loading…