Trifluoroacetic acid → tert-Butyl (3S)-3-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-1-carboxylate

HRID 330916Notes

Reaction equation

HRID 330916 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][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:11])[N:3]1[O:24]S(O)(=O)=O.F[C:30](F)(F)[C:31](O)=O>C(Cl)Cl>[OH:24][N:3]1[C:2](=[O:1])[N:8]2[CH2:9][C@H:4]1[CH2:5][CH2:6][C@H:7]2[C:10]([NH:12][O:13][C@H:14]1[CH2:31][CH2:30][N:16]([C:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:23])[CH2:15]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699592tert-Butyl {2-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate

Product 1

HCID 86693916tert-Butyl (3S)-3-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tert-butyl {2-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate 44 (0.19 g, 0.45 mmol) in DCM (6.0 mL) was added trifluoroacetic acid (0.30 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, concentrated and washed with ether. The white solid was collected by centrifugation. The crude product was purified by preparative HPLC to provide Compound 9 (Table 1) (44 mg) as a white solid.

Workup

  1. concentrationconcentrated
  2. washwashed with ether
  3. customThe white solid was collected by centrifugation
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ff1e4e55b0474e7c81c1318d28e4a474
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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