Trifluoroacetic acid → 1174018-99-5

HRID 451295Notes

Reaction equation

HRID 451295 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][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])[N:3]1[O:19][S:20]([O-:23])(=[O:22])=[O:21].C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O>ClCCl>[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][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])[N:3]1[O:19][S:20]([OH:23])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659583HCID 86659583, compound

Product 1

HCID 441296471174018-99-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N-tributylbutan-1-aminium [({(2S,5R)-7-oxo-2-[(piperidin-4-ylamino)carbonyl]-1,6-diazabicyclo[3.2.1]oct-6-yl}oxy)sulfonyl]oxidanide (22.4 mg, 0.050 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under nitrogen was added trifluoroacetic acid (0.1 mL, 1.298 mmol) dropwise. The reaction mixture was stirred for 1 hour then concentrated under vacuum. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The solid was washed with ether (2× to afford the title compound contaminated with tetrabutylammonium hydrogen sulfate and pyridine. The solid was triturated with acetonitrile (2×) and the white solid was collected by centrifugation to afford the title compound as a white solid. LC-MS (negative ionization) m/e 347 (M−H); LC-MS (positive ionization) m/e 349 (M+H), 381 (M+Na); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 4.19 (1H, br d, J=2.5 Hz), 3.98-4.06 (2H, m), 3.47 (2H, br d, J=13 Hz), 3.31 (1H, br d, J=12 Hz), 3.12 (2H, br dd, J=13, 3 Hz), 3.06 (1H, d, J==12 Hz), 2.04-2.21 (m, 4H), 1.87-1.95 (1H, m), 1.72-1.83 (m, 3H).

Workup

  1. concentrationthen concentrated under vacuum
  2. additionEther was added to the residue
  3. customthe resulting white precipitate was collected by centrifugation
  4. washThe solid was washed with ether (2×

Sources & evidence

ORD record
ord-78479ac7c54a4b16ac515e6d4cc5f62a
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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