Trifluoroacetic acid → (1R,2S,5R)-2-[[[(4S)-Hexahydro-1H-azepin-4-yl]amino]carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl hydrogen sulfate

HRID 451303Notes

Reaction equation

HRID 451303 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:24])[N:14]3[O:19][S:20]([O-:23])(=[O:22])=[O:21])=[O:10])[CH2:3][CH2:2]1.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>ClCCl>[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:24])[N:14]3[O:19][S:20]([OH:23])(=[O:21])=[O:22])=[O:10])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659587HCID 86659587, compound

Product 1

HCID 44183767(1R,2S,5R)-2-[[[(4S)-Hexahydro-1H-azepin-4-yl]amino]carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N-tributylbutan-1-aminium {[((2S,5R)-2-{[(4S)-azepan-4-ylamino]carbonyl}-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl)oxy]sulfonyl}oxidanide (30.9 mg, 0.067 mmol) in anhydrous dichloromethane (7 mL) at 0° C. under nitrogen was added trifluoroacetic acid (0.5 mL, 6.5 mmol) dropwise. The reaction mixture was stirred for two hours then concentrated under vacuum. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The precipitate was purified by HPLC on a Phenomenex Synergy Polar-RP 80A column and lyophilized to afford the title compound as a white solid. LC-MS (negative ionization) m/e 361 (M−H); LC-MS (positive ionization) m/e 385 (M+Na); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 4.17 (1H, br d, J=3 Hz), 3.96-4.03 (2H, m), 3.27-3.38 (3H, m), 3.15-3.22 (2H, m), 3.02 (1H, d, J=12 Hz), 1.62-2.18 (m, 12H).

Workup

  1. concentrationthen concentrated under vacuum
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. customThe precipitate was purified by HPLC on a Phenomenex Synergy Polar-RP 80A column

Sources & evidence

ORD record
ord-9d7899519cb24cdca09d3c3a8824f350
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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