Methanesulfonyl chloride → HCID 21994022, compound

HRID 1978361Notes

Reaction equation

HRID 1978361 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.C(=O)([O-])O.[Na+].S([O-])(=O)(=O)C.[C:33]1([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.C(O)C.O.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:42]2[CH2:43][CH2:44][CH:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:40][CH2:41]2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 5

HCID 31297Methanesulfonyl chlorideHCID 698734-PhenylpiperidineHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

Product 1

HCID 21994022HCID 21994022, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

To a solution of 5.0 g (21.07 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]-1-phenylmethanol and 5.9 ml (42.33 mM) of triethylamine in THF (42 ml) was added 2.5 ml (32.3 mM) of methanesulfonyl chloride at 0° C. and the mixture was stirred at the prevailing temperature for one hour. The reaction was then stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 6.72 g (21.07 mM) of crude product as light-brown solid. To a solution of 6.72 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 ml (42.33 mM) of triethylamine as well as 3.40 g (21.09 mM) of 4-phenylpiperidine and the mixture was refluxed for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customto provide 6.72 g (21.07 mM) of crude product as light-brown solid
  6. temperaturethe mixture was refluxed for 18 hours
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationAfter concentration
  11. customthe crude product was purified by column chromatography (ethyl acetate-hexane: 50%)

Sources & evidence

ORD record
ord-ecdcd3961e294cde87aa669fb70b01e5
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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