Diethylamine → HCID 86700695, compound

HRID 1406876Notes

Reaction equation

HRID 1406876 reaction equation
N(CC)CC.S([O-])([O-])(=O)=O.C1C2C(COC([N:28]3[CH2:33][CH2:32][CH:31]([C:34]4[N:38]=[C:37]([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])[O:36][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:37]1[O:36][N:35]=[C:34]([CH:31]2[CH2:32][CH2:33][NH:28][CH2:29][CH2:30]2)[N:38]=1)(=[O:49])=[O:50]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86700696HCID 86700696, compound

Product 1

HCID 86700695HCID 86700695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et2NH (6.1 mL, 60.0 mmol) was added to a solution of tetrabutylammonium (9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-7-oxo-6-(sulfooxy)-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate sulfate (1.0 g, 1.2 mmol) in dried CH2Cl2 (30 mL). The mixture was stirred under N2 atmosphere at rt. for 12 hrs, then evaporated under vacuum. The residue was purified by prep-HPLC using the ammonium formate conditions. E SI-MS (EI+, m/z): 314.2. 1H NMR (300 MHz, D2O) δ 4.82 (d, J=8.0 Hz, 1H), 4.17 (br s, 1H), 3.47-3.45 (m, 2H), 3.25-3.12 (m, 3H), 2.96-2.92 (m, 1H), 2.39-1.94 (m, 8H).

Workup

  1. customevaporated under vacuum
  2. customThe residue was purified

Sources & evidence

ORD record
ord-5399bbbb7404454a861d15c5a83d7fec
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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