Diethylamine → HCID 71291193, compound

HRID 1406865Notes

Reaction equation

HRID 1406865 reaction equation
N(CC)CC.S([O-])([O-])(=O)=O.C1C2C(COC([N:28]3[CH2:33][CH2:32][CH:31]([C:34]4[O:38][N:37]=[C:36]([C@@H:39]5[CH2:45][CH2:44][C@@H:43]6[CH2:46][N:40]5[C:41](=[O:52])[N:42]6[O:47][S:48]([OH:51])(=[O:50])=[O:49])[N:35]=4)[CH2:30][CH2:29]3)=O)C3C(=CC=CC=3)C=2C=CC=1.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[S:48]([OH:51])([O:47][N:42]1[C:41](=[O:52])[N:40]2[CH2:46][C@H:43]1[CH2:44][CH2:45][C@H:39]2[C:36]1[N:35]=[C:34]([CH:31]2[CH2:32][CH2:33][NH:28][CH2:29][CH2:30]2)[O:38][N:37]=1)(=[O:49])=[O:50]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86700683HCID 86700683, compound

Product 1

HCID 71291193HCID 71291193, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et2NH (0.5 mL, 5.0 mmol)) was added to a solution of tetrabutylammonium (9H-fluoren-9-yl)methyl 4-(3-((2S,5R)-7-oxo-6-(sulfooxy)-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate sulfate (84 mg, 0.1 mmol) in dry DCM (10 mL. The mixture was stirred at rt for 12 hrs and the solvents were evaporated under vacuum. The residue was purified by prep-HPLC to afford (2S,5R)-7-oxo-2-(5-(piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-1,6-diaza-bicyclo[3.2.1]octan-6-yl hydrogen sulfate (9.0 mg). ESI-MS (EI+, m/z): 374.15 [M+H]+. 1H NMR (300 MHz, D2O) δ 4.61 (d, J=6.0 Hz, 1H), 4.12 (br s, 1H), 3.50-3.33 (m, 3H), 3.15-3.05 (m, 3H), 2.91 (d, J=12.2 Hz, 1H), 2.35-1.72 (m, 8H).

Workup

  1. customthe solvents were evaporated under vacuum
  2. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-99c7b50562f546f6a41d4eda9ff929f6
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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