Ethyl Acetate → HCID 59287096, compound

HRID 2045712Notes

Reaction equation

HRID 2045712 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[C:9](=[O:20])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2.BrC1C=CC(S(O[C@@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)(=O)=O)=CC=1.CCOC(C)=O>CN1C(=O)CCC1.O>[Br:7][C:8]1[C:9]([O:20][C@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=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-dicarboxylateHCID 59287022HCID 59287022, compound

Product 1

HCID 59287096HCID 59287096, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

Cs2CO3 (2.11 g, 6.46 mmol) was added to a solution of 3-bromo-7-methoxyquinolin-2(1H)-one (1.31 g, 5.17 mmol) and 1-text-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), and the reaction mixture was stirred for 40 h at 40° C. An additional portion of 1-tert-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 h. The reaction mixture was cooled and poured onto a mixture of EtOAc and water, and the layers were separated. The organic layer was washed with water twice, NaHCO3 twice 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 h
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. washThe organic layer was washed with water twice
  5. dry with materialNaHCO3 twice and brine, dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was used with no further purification

Sources & evidence

ORD record
ord-3a1ea12aedf74109bc27aa6c6b901734
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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