Trifluoroacetic acid → HCID 78426341, compound

HRID 1053434Notes

Reaction equation

HRID 1053434 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][N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[O:11])[N:3]1[O:26][S:27]([OH:30])(=[O:29])=[O:28].FC(F)(F)C(O)=O>C(Cl)Cl>[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][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])[N:3]1[O:26][S:27]([OH:30])(=[O:28])=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694049HCID 86694049, compound

Product 1

HCID 78426341HCID 78426341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)piperazine-1-carboxylate 208 (0.12 g, 0.27 mmol) in DCM (12.5 mL) was added trifluoroacetic acid (1.0 mL, 12.96 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. This white solid was purified by HPLC on a prep-X Bridge-19×250 mm column and freeze-dried to give (2S,5R)-7-oxo-N-(piperazin-1-yl)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Compound 100 (Table 2) (0.11 g, 88%) 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. customThis white solid was purified by HPLC on a prep-X Bridge-19×250 mm column
  7. customfreeze-dried

Sources & evidence

ORD record
ord-0913ba3a2e1e46698d5ba57878e36466
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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