Acetonitrile → HCID 16122922, compound

HRID 1397825Notes

Reaction equation

HRID 1397825 reaction equation
[O:1]=[C:2]1[C@@H:8]2[C@@H:4]([CH2:5][CH2:6][NH:7]2)[N:3]1[S:9]([OH:12])(=[O:11])=[O:10].CC#N.C([O-])(O)=O.[Na+].[NH2:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](ON2C(=O)CCC2=O)=[O:36])=[CH:30][CH:29]=1)=[O:26]>O>[NH2:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([N:7]2[CH2:6][CH2:5][C@@H:4]3[C@H:8]2[C:2](=[O:1])[N:3]3[S:9]([OH:12])(=[O:11])=[O:10])=[O:36])=[CH:30][CH:29]=1)=[O:26]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 10583895HCID 10583895, compound2×HCID 131730602HCID 131730602, compound

Product 1

HCID 16122922HCID 16122922, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1S,5R)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid (compound H, 2.0 g, 10.41 mmol, 1.0 eq) was dissolved in H2O (12.5 mL). Then CH3CN (100 mL) was added at room temperature to the solution, followed by NaHCO3 (1.57 g, 18.73 mmol, 1.8 eq) and [(2-aminoethyl)amino]-N-{4-[(2,5-dioxoazolidinyloxy)carbonylamino]phenyl}carboxamide (6.89 g, 14.57 mmol, 1.4 eq). After stirring overnight at room temperature, the reaction mixture was filtered to afford 3.27 g of the expected (1S,5R)-2-[N-(4-{[(2-aminoethyl)amino]carbonylamino}phenyl)carbamoyl]-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-94a23154df7f446e8e42443fa3d0dbdd
Source dataset
uspto-grants-2014_12
Patent number
US08901293B2

Reaction notes

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