Cesium carbonate → HCID 54684213, compound

HRID 1013008Notes

Reaction equation

HRID 1013008 reaction equation
ClCS([O:6][C:7]1[C:8]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[O:24])=[N:9][C:10]([C:14]([NH:17][S:18]([CH2:21]Cl)(=[O:20])=[O:19])([CH3:16])[CH3:15])=[N:11][C:12]=1[OH:13])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][NH:25][C:23]([C:8]2[N:9]=[C:10]3[N:11]([C:12](=[O:13])[C:7]=2[OH:6])[CH2:21][S:18](=[O:19])(=[O:20])[NH:17][C:14]3([CH3:16])[CH3:15])=[O:24])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 178458106HCID 178458106, compound

Product 1

HCID 54684213HCID 54684213, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Crude chloride of Step 1 was dissolved in 1,4-dioxane and Cs2CO3 (2 eq.) was added. The reaction mixture was stirred at 100° C. overnight, then cooled down to room temperature, taken up in EtOAc washed with brine, dried over Na2SO4. The solvent was removed under reduced pressure and the resulting brown oil was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant). Lyophilization of appropriate fractions gave title compound as a white solid.

Workup

  1. temperaturecooled down to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting brown oil was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-f0668ad81712494d839ae597e39d6807
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

Loading…