Acetonitrile → HCID 16122922, compound

HRID 2098274Notes

Reaction equation

HRID 2098274 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 B of Reaction Scheme 2, 2.0 g, 10.41 mmol, 1.0 eq) is dissolved in H2O (12.5 mL). Then CH3CN (100 mL) is 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 (Compound C-1) (6.89 g, 14.57 mmol, 1.4 eq). After stirring overnight at room temperature, the reaction mixture is 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 is filtered

Sources & evidence

ORD record
ord-20a1d922695a4c56b0616a549d463785
Source dataset
uspto-grants-2013_05
Patent number
US08450477B2

Reaction notes

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