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 2400624Notes

Reaction equation

HRID 2400624 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][O:10][NH:11][C:12]([C@@H:14]1[CH2:20][CH2:19][C@@H:18]2[CH2:21][N:15]1[C:16](=[O:27])[N:17]2[O:22]S(O)(=O)=O)=[O:13])([CH3:4])([CH3:3])[CH3:2].F[C:30](F)(F)[C:31](O)=O>C(Cl)Cl>[OH:22][N:17]1[C:16](=[O:27])[N:15]2[CH2:21][C@H:18]1[CH2:19][CH2:20][C@H:14]2[C:12]([NH:11][O:10][C@H:9]1[CH2:31][CH2:30][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])[CH2:8]1)=[O:13]

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-c4dd035e21aa4a36806635bb65eb6da1
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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