Pyridine → HCID 86700997, compound

HRID 1430659Notes

Reaction equation

HRID 1430659 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 −10° C. 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) 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 slightly 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-22781138b049419d9d8025699e63bbd1
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

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