Trifluoroacetic acid → HCID 86694091, compound

HRID 2400747Notes

Reaction equation

HRID 2400747 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][NH:13][C:14]([C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2C(OC(C)(C)C)=O)=[O:15])=[O:11])[N:3]1[O:29][S:30]([OH:33])(=[O:32])=[O:31].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][NH:13][C:14]([C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][NH:17]2)=[O:15])=[O:11])[N:3]1[O:29][S:30]([OH:33])(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694090HCID 86694090, compound

Product 1

HCID 86694091HCID 86694091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution tert-butyl (2S)-2-[(2-{[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}hydrazinyl)carbonyl]piperidine-1-carboxylate 273 (0.30 g, 0.61 mmol) in DCM (30 mL) was added trifluoroacetic acid (2.42 mL, 31.38 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 a mixture of MeOH:ether (1:5, 6×) and the white solid was collected by centrifugation to give (2S,5R)-7-oxo-N′-[(2S)-piperidin-2-ylcarbonyl]-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide Compound 43 (Table 2) (0.09 g, 38%) as a white solid.

Workup

  1. customthen evaporated
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe solid was triturated with a mixture of MeOH:ether (1:5, 6×)
  5. customthe white solid was collected by centrifugation

Sources & evidence

ORD record
ord-f07df8f2fd4d4e8c993cb582ee0c24ec
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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