Potassium Carbonate → HCID 86649573, compound

HRID 1964669Notes

Reaction equation

HRID 1964669 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:45][CH3:46])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([NH:30][C@H:31]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[C@@H:32]([CH3:34])[OH:33])=O)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1.COCCN(S(F)(F)F)CCOC.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][O:2][CH2:3][C@@H:4]([O:45][CH3:46])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:33][C@@H:32]([CH3:34])[C@@H:31]([C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])[N:30]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 66681470HCID 66681470, compound

Product 1

HCID 86649573HCID 86649573, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Benzyl N-{[5-(3-[(1S)-2-methoxy-1-methoxyethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrol-2-yl]carbonyl}-L-threoninate (13.5 g, 21.2 mmol) synthesized in Example (103b) was dissolved in methylene chloride (150 mL), and cooled to −78° C. Bis(2-methoxyethyl)amino sulfur trifluoride (5.47 mL, 29.7 mmol) was added dropwise, and stirring was carried out at −78° C. for 40 minutes. Potassium carbonate (5.86 g, 42.4 mmol) was added, and stirring was carried out for 1.5 hours with the temperature being raised gradually to room temperature. A saturated aqueous sodium hydrogencarbonate solution (100 mL) was added at 0° C., and extraction was carried out twice with methylene chloride (100 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-70%) to afford the desired product (9.68 g, yield 74%) as a white solid.

Workup

  1. stirringstirring
  2. waitwas carried out for 1.5 hours with the temperature
  3. temperaturebeing raised gradually to room temperature
  4. extractionextraction
  5. washThe organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified
  9. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-70%)

Sources & evidence

ORD record
ord-5270c65e5dcd42ca99086f3a96f6f663
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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