Water → HCID 67243482, compound

HRID 1436031Notes

Reaction equation

HRID 1436031 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].O.[C:32](OCC)(=[O:34])C>CO.N1C=CC=CC=1.[Cu](I)I>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([O:34][CH3:32])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67242856(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67243482HCID 67243482, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 887MethanolSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of Intermediate 1 (337 mg) obtained in Example 1, Step A in methanol (2.7 ml) and pyridine (2.7 ml) is added with a solution of 28% sodium methylate (847 mg) in methanol, and then with copper iodide (70 mg), and the mixture is stirred at 65° C. for 30 hours. The reaction mixture is cooled to room temperature, and added with water (30 ml) and ethyl acetate (30 ml), and the insoluble matters are removed by filtration through Celite. The organic layer of the filtrate is separated, and the aqueous layer is extracted 3 times with ethyl acetate (20 ml for each time). The combined organic layer is washed 3 times with saturated brine (30 ml for each time), and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound (98 mg (predictive yield)).

Workup

  1. customthe insoluble matters are removed by filtration through Celite
  2. customThe organic layer of the filtrate is separated
  3. extractionthe aqueous layer is extracted 3 times with ethyl acetate (20 ml for each time)
  4. washThe combined organic layer is washed 3 times with saturated brine (30 ml for each time), and
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue is purified by silica gel chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-4c3d25e2d2d44442bbb8b32ad5168db3
Source dataset
uspto-grants-2009_11
Patent number
US07618984B2

Reaction notes

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