Trifluoroacetic acid → HCID 86693949, compound

HRID 2400627Notes

Reaction equation

HRID 2400627 reaction equation
[O:1]=[C:2]1[N:8]2[CH2:9][C@@H:4]([CH2:5][CH2:6][C@H:7]2[C:10]([NH:12][O:13][CH:14]2[CH2:20][CH:19]3[N:21](C(OC(C)(C)C)=O)[CH:16]([CH2:17][CH2:18]3)[CH2:15]2)=[O:11])[N:3]1[O:29][S:30]([OH:33])(=[O:32])=[O:31].FC(F)(F)C(O)=O>C(Cl)Cl>[CH:16]12[NH:21][CH:19]([CH2:18][CH2:17]1)[CH2:20][CH:14]([O:13][NH:12][C:10]([C@@H:7]1[CH2:6][CH2:5][C@@H:4]3[CH2:9][N:8]1[C:2](=[O:1])[N:3]3[O:29][S:30]([OH:33])(=[O:32])=[O:31])=[O:11])[CH2:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86693948HCID 86693948, compound

Product 1

HCID 86693949HCID 86693949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]-8-azabicyclo[3.2.1]octane-8-carboxylate 48 (0.077 g, 0.17 mmol) in DCM (7 mL) was added trifluoroacetic acid (0.34 mL, 4.42 mmol) dropwise at 0° C. The reaction mixture was stirred for 1 h, then 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-(8-azabicyclo[3.2.1]oct-3-yloxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Compound 27 (Table 1) (0.003 g, 7%) as a white solid.

Workup

  1. customevaporated
  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-b8627cba31e54363808976bb5e3f6718
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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