Trifluoroacetic acid → HCID 73386853, compound

HRID 330894Notes

Reaction equation

HRID 330894 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][NH:14][C:15]([C@@H:17]2[CH2:23][CH2:22][C@@H:21]3[CH2:24][N:18]2[C:19](=[O:30])[N:20]3[O:25][S:26]([O-:29])(=[O:28])=[O:27])=[O:16])[CH2:9]1)=O)(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>C(Cl)Cl>[O:30]=[C:19]1[N:18]2[CH2:24][C@@H:21]([CH2:22][CH2:23][C@H:17]2[C:15]([NH:14][O:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:16])[N:20]1[O:25][S:26]([OH:29])(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86693915HCID 86693915, compound

Product 1

HCID 73386853HCID 73386853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N-tributylbutan-1-aminium ({[(2S,5R)-2-({[(3R)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}carbamoyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulfonyl)oxidanide 6 (0.245 g, 0.35 mmol) in DCM (14 mL) was added trifluoroacetic acid (0.70 mL, 9.08 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 on a prep-X Bridge-19×250 mm column and freeze-dried to give (2S,5R)-7-oxo-N-[(3R)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Compound 1 (Table 1) (0.03 g, 25%) 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 on a prep-X Bridge-19×250 mm column
  7. customfreeze-dried

Sources & evidence

ORD record
ord-962629b4f8c648bb9a53fddc04ed1f3f
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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