Ethyl Acetate → HCID 59287096, compound

HRID 389211Notes

Reaction equation

HRID 389211 reaction equation
[Br:1][C:2]1[C:3](=[O:14])[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.BrC1C=CC(S(O[C@@H:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH2:27]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN1C(=O)CCC1.O>[Br:1][C:2]1[C:3]([O:14][C@H:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH2:27]2)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2

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 59287022HCID 59287022, compound

Product 1

HCID 59287096HCID 59287096, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-bromo-7-methoxyquinolin-2(1H)-one (1.31 g, 5.17 mmol) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (2.0 g, 4.31 mmol) in NMP (21.5 mL), Cs2CO3 (2.11 g, 6.46 mmol) was added, and the reaction mixture was stirred for 40 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×), NaHCO3 (2×) and brine, dried over Mg2SO4, filtered and concentrated. The product was used with no further purification. LRMS (M+H-Boc)+=381.2.

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×), NaHCO3 (2×) and brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was used with no further purification

Sources & evidence

ORD record
ord-8908648a477f4f618a4a1fe9e6869c0d
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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