Pyridine → HCID 23302078, compound

HRID 1952978Notes

Reaction equation

HRID 1952978 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][CH2:19]O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][CH2:19][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22006367tert-Butyl benzyl(4-hydroxybutyl)carbamate

Product 1

HCID 23302078HCID 23302078, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Cool a mixture of 4-[N-(t-butoxycarbonyl)-N-[(phenyl)methyl]-amino]butan-1-ol (21.8 g, 0.078 mol), methylene chloride (250 mL) and pyridine (9.7 mL). Add mesylchloride (6.65 mL, 0.086 mol) in methylene chloride (6.6 mL) dropwise to the reaction with stirring. After addition is complete, allow the reaction to warm to room temperature and stir for an additional 2 hours. Pour the reaction into methylene chloride (200 mL), rinse with 0.5 N hydrochloric acid (500 mL), saturated sodium bicarbonate (500 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (25% ethyl acetate/hexane, silica gel) to provide 4-[N-(t-butoxycarbonyl)-N-[(phenyl)methyl]-amino]-1-methansulfonyl butane (10.7 g), Rf =0.36 eluting with 25% ethyl acetate/hexane.

Workup

  1. temperatureCool
  2. additionAfter addition
  3. customthe reaction
  4. stirringstir for an additional 2 hours
  5. additionPour
  6. washrinse with 0.5 N hydrochloric acid (500 mL), saturated sodium bicarbonate (500 mL)
  7. dry with materialdry over anhydrous magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum
  10. customPurify the residue by flash chromatography (25% ethyl acetate/hexane, silica gel)

Sources & evidence

ORD record
ord-2b1fbdd24bea40898c95adaa0c7090bc
Source dataset
uspto-grants-2000_09
Patent number
US06114394

Reaction notes

Loading…