Pyridine → HCID 23302078, compound

HRID 1291723Notes

Reaction equation

HRID 1291723 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Cool (ice-bath) a mixture containing the product of Step C (21.8 gm - 0.078 mol), 250 ml CH2Cl2 and 9.7 ml pyridine (0.12 mol), add in a dropwise fashion (20 minutes) mesylchloride (6.65 ml - 0.086 mol) in 6.6 ml CH2Cl2 and allow the mixture to warm to room temperature, stirring the mixture for 2 hours. Pour the resulting mixture into 200 ml CH2Cl2, wash with 500 ml 0.5N HCl, saturated NaHCO3, dry over MgSO4, evaporate (in vacuo) and flash chromatograph eluting from the silica gel with 25% EtOAc/hexane to obtain 10.7 g of desired product, Rf is 0.36 (silica gel plates eluted with 25% EtOAc/hexane).

Workup

  1. temperatureCool (ice-bath) a mixture
  2. washwash with 500 ml 0.5N HCl, saturated NaHCO3
  3. dry with materialdry over MgSO4
  4. customevaporate (in vacuo) and flash chromatograph
  5. washeluting from the silica gel with 25% EtOAc/hexane
  6. customto obtain
  7. wash10.7 g of desired product, Rf is 0.36 (silica gel plates eluted with 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-208974c1a3894ae59b9d96fc33d3551b
Source dataset
uspto-grants-1998_05
Patent number
US05753714

Reaction notes

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