Methanesulfonyl chloride → HCID 22004847, compound

HRID 324651Notes

Reaction equation

HRID 324651 reaction equation
[CH:1]([N:3]1[C:11]2[C:6](=[C:7]([CH2:13][CH2:14][OH:15])[C:8](O)=[CH:9][CH:10]=2)[CH:5]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:4]1)=[O:2].CS(Cl)(=O)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[CH:1]([N:3]1[C:11]2[C:6](=[C:7]3[CH2:13][CH2:14][O:15][C:8]3=[CH:9][CH:10]=2)[CH:5]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:4]1)=[O:2]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 22004824HCID 22004824, compound

Product 1

HCID 22004847HCID 22004847, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[2-[1-formyl-2,3-dihydro-5-hydroxy-4-(2-hydroxyethyl)indol-3-yl]ethyl]propionamide (0.8 g, 2.61 mmol) in pyridine (10 mL) was added methansulfonyl chloride (0.2 mL, 2.61 mmol.) around −10° C. The mixture was stirred for 20 minutes while keeping the temperature −10 to 5° C. To this was added additional methansulfonyl chloride (0.1 mL, 1.3 mmol.) and the mixture was stirred for further 15 minutes at the same temperature. The mixture was diluted with ethyl acetate(10 mL). Saturated aqueous sodium hydrogen carbonate solution (10 mL) was added slowly and the mixture was stirred for 30 minutes at room temperature. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 2N-hydrochloric acid and water, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to afford the title compound (yield 0.25 g, 33%).

Workup

  1. customthe temperature −10 to 5° C
  2. stirringthe mixture was stirred for further 15 minutes at the same temperature
  3. stirringthe mixture was stirred for 30 minutes at room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with 2N-hydrochloric acid and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-5f9adad0e2f94f40a126e5ea1f594f54
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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