Trifluoroacetic acid → HCID 71291373, compound

HRID 2400697Notes

Reaction equation

HRID 2400697 reaction equation
C(O[C:6]([N:8](C)[NH:9][C:10]([C@@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][N:13]1[C:14](=[O:25])[N:15]2[O:20][S:21]([O-:24])(=[O:23])=[O:22])=[O:11])=O)(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:6][NH:8][NH:9][C:10]([C@@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][N:13]1[C:14](=[O:25])[N:15]2[O:20][S:21]([OH:24])(=[O:23])=[O:22])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694027HCID 86694027, compound

Product 1

HCID 71291373HCID 71291373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N-tributylbutan-1-aminium({[(2S,5R)-2-{[2-(tert-butoxycarbonyl)-2-methylhydrazinyl]carbonyl}-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulfonyl)oxidanide 180 (0.31 g, 0.49 mmol) in DCM (20 mL) was added trifluoroacetic acid (1.2 mL, 15.55 mmol) dropwise at 0° C. The reaction mixture was stirred for 2 h, than evaporated. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The solid was triturated with acetonitrile (2×) and the white solid was collected by centrifugation. The white solid was purified by HPLC and freeze-dried to give (2S,5R)—N′-methyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide Compound 1 (Table 2) (0.01 g, 6.9%) as a white solid.

Workup

  1. customthan evaporated
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe solid was triturated with acetonitrile (2×)
  5. customthe white solid was collected by centrifugation
  6. customThe white solid was purified by HPLC
  7. customfreeze-dried

Sources & evidence

ORD record
ord-122d47b34f0544ecb9a35eafa87e7cbb
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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