Ethyl Acetate → HCID 58157992, compound

HRID 1255517Notes

Reaction equation

HRID 1255517 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([N:11]1[C:20](=[O:21])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:22])[CH2:8][CH:9]=[CH2:10].BrC1C=CC(S(O[C@@H:34]2[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:36]([C:46]([O:48][CH3:49])=[O:47])[CH2:35]2)(=O)=O)=CC=1.CCOC(C)=O>CN1C(=O)CCC1.O>[CH2:7]([N:11]1[C:20]([O:21][C@H:34]2[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:36]([C:46]([O:48][CH3:49])=[O:47])[CH2:35]2)=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:22])[CH2:8][CH:9]=[CH2:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate2×HCID 58158002HCID 58158002, compound

Product 1

HCID 58157992HCID 58157992, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

Cs2CO3 (1.1 g, 3.39 mmol) was added to a solution of 2-but-3-en-1-ylisoquinoline-1,3(2H,4H)-dione (0.49 g, 2.26 mmol) and 1-t-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.05 g, 2.26 mmol) in NMP (10 mL), and the reaction mixture was stirred for 16 hours at 40° C. An additional portion of 1-t-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.0 g, 2.16 mmol) was added, and the reaction mixture was stirred at 40° C. for 16 hours. The reaction mixture was cooled and poured onto a mixture of EtOAc and H2O, and the layers were separated. The organic layer was washed with H2O (2×), 1N HCl (1×) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient elution, 10-40% EtOAc/Hexane) to afford the title compound (0.83 g, 83%) as an oil. LCMS (ES+) m/z 443.0 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. washThe organic layer was washed with H2O (2×), 1N HCl (1×) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (gradient elution, 10-40% EtOAc/Hexane)

Sources & evidence

ORD record
ord-48ab6f855e704baab19aeb4db862982f
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

Loading…