Pyridine → HCID 86700997, compound

HRID 2272853Notes

Reaction equation

HRID 2272853 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][CH:22]=[O:23])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[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[O:23][CH:22]=[N:21][N:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86700996HCID 86700996, compound

Product 1

HCID 86700997HCID 86700997, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,5R)-6-(benzyloxy)-N′-formyl-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (11 g) in dry DCM (200 mL) at −10° C. was added pyridine (28 mL), followed by dropwise addition of (CF3SO2)2O (28 mL). The reaction mixture was allowed to warm to rt and was stirred for 3 hrs. The reaction mixture was then cooled to −10° C. and quenched with sat. NaHCO3. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography (gradient elution 1:3 to 2:1 EtOAc/hexanes) to give (2S,5R)-6-(benzyloxy)-2-(1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (4.6 g, 86% for two steps) as a slight yellow solid. ESI-MS (EI+, m/z): 301.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was then cooled to −10° C.
  2. customquenched with sat. NaHCO3
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (gradient elution 1:3 to 2:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-f73b703c8f01450fbcc5ff89ec3aecd6
Source dataset
uspto-grants-2015_09
Patent number
US09120795B2

Reaction notes

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