Cesium carbonate → HCID 58196034, compound

HRID 1258133Notes

Reaction equation

HRID 1258133 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:28])[C:10]([N:16]1[CH2:18][CH:17]1[C:19]1[CH:27]=[CH:26][C:22]2[O:23][CH2:24][O:25][C:21]=2[CH:20]=1)=[CH:11][C:12]([O:14][CH3:15])=[O:13]>O1CCOCC1>[CH3:7][O:8][C:9]([C:10]1[NH:16][CH:18]=[C:17]([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)[C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:28]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 76721669HCID 76721669, compound

Product 1

HCID 58196034HCID 58196034, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (110 mg, 0.30 mmol, 4.0 equiv) was added to a stirred solution of aziridine 26 (25 mg, 82 μmol, 1.0 equiv) in 1,4-dioxane (12 mL) at 25° C. The reaction vessel was sealed under argon and heated to 100° C. via oil bath for 20 h. The reaction mixture was cooled to 25° C., gravity filtered, and concentrated by rotary evaporation to afford 27 (23 mg, 92% yield) as a dark orange film. 1H NMR (500 MHz, CDCl3) δ 10.22 (br d, 1H, J=11 Hz, NH), 7.43 (dd, 1H, J=14, 11 Hz, pyrrole H), 6.80 (d, 1H, J=1.5 Hz, ArH), 6.72 (d, 1H, J=8 Hz, ArH), 6.69 (dd, 1H, J=8, 1.5 Hz, ArH), 5.93 (s, 2H, OCH2O), 3.89 (s, 3H, OCH3), 3.73 (s, 3H, OCH3); IR (neat film) 3348 (w, br), 2944 (w), 2890 (w), 1731 (m), 1651 (s), 1608 (s), 1503 (m), 1484 (m), 1444 (m) cm−1; HRMS (ESI) m/z: Calcd for C15H14NO6 (MH+) 304.0821; observed 304.0815.

Workup

  1. customThe reaction vessel was sealed under argon
  2. temperatureThe reaction mixture was cooled to 25° C.
  3. filtrationgravity filtered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-797cc5af98e64bd387d0d605f0615600
Source dataset
uspto-grants-2013_06
Patent number
US08466142B2

Reaction notes

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