Pyridine → HCID 23302078, compound

HRID 862782Notes

Reaction equation

HRID 862782 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-50b3d2d83e9440ef82355d41c151be4b
Source dataset
uspto-grants-1998_02
Patent number
US05719193

Reaction notes

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