Trifluoroacetic acid → HCID 71761253, compound

HRID 1427635Notes

Reaction equation

HRID 1427635 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[O:22][C:23]([C@@H:26]3[CH2:32][CH2:31][C@@H:30]4[CH2:33][N:27]3[C:28](=[O:39])[N:29]4[O:34][S:35]([OH:38])(=[O:37])=[O:36])=[N:24][N:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CCOCC>[S:35]([OH:38])([O:34][N:29]1[C:28](=[O:39])[N:27]2[CH2:33][C@H:30]1[CH2:31][CH2:32][C@H:26]2[C:23]1[O:22][C:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[N:25][N:24]=1)(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86701007HCID 86701007, compound

Product 1

HCID 71761253HCID 71761253, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TFA (0.30 mL) was added to a 0° C. mixture of tetrabutylammonium tert-butyl 4-(5-((2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)piperazine-1-carboxylate (21 mg, 0.03 mmol) in dry DCM (0.80 mL). The reaction mixture was stirred at 0° C. for 2-3 hrs then diluted with ether (−15 mL). The precipitate was collected via centrifugation, washed with ether (3×) and dried under high vacuum to afford (2S,5R)-7-oxo-2-(5-(piperazin-1-yl)-1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate (4 mg, 35%) as a light yellow solid after prep-HPLC purification using ammonium formate buffer. ESI-MS (EI+, m/z): 375.2. 1H NMR (300 MHz, D2O) δ 4.65 (d, J=6.6 Hz, 1H), 4.19 (br s, 1H), 3.80-3.65 (m, 2H), 3.38-3.28 (m, 2H), 3.20-3.16 (m, 1H), 2.99-2.95 (m, 1H), 2.32-1.88 (m, 4H).

Workup

  1. customThe precipitate was collected via centrifugation
  2. washwashed with ether (3×)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-1f3ec468902d45e3845ba2aa4ba1165f
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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