4-Toluenesulfonyl chloride → HCID 71496931, compound

HRID 1695304Notes

Reaction equation

HRID 1695304 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=[C:15]([CH2:21][OH:22])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[K+].[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>ClCCl.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][O:20][S:25]([C:28]2[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[N:16]=[C:15]([CH2:21][O:22][S:25]([C:28]2[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=2)(=[O:26])=[O:23])[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 57570973HCID 57570973, compound

Product 1

HCID 71496931HCID 71496931, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a precooled (0° C.) solution of 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(hydroxymethyl)-pyridine (76 mg) in dichloromethane (0.7 mL), was added a solution of potassium hydroxide (30 mg) in water (0.3 mL). Tosyl chloride (93.7 mg) was added, and the resulting heterogenous mixture was shaken vigorously for 1 h and then washed into separatory funnel using dichloromethane and water. The layers were separated, and the aqueous layer was extracted three times with dichloromethane. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Interchrom Puriflash 10 g column, SiOH 15-35 μm), using gradient elution with a mixture of heptane (A) and ethyl acetate (B) (gradient: 90% A:10% B up to 50% A:50% B) to give 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(tosyloxymethyl)pyridine (56 mg):

Workup

  1. washwashed into separatory funnel
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic solutions were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a residue
  6. customThe residue was purified by silica gel chromatography (Interchrom Puriflash 10 g column, SiOH 15-35 μm)
  7. washelution
  8. additionwith a mixture of heptane (A) and ethyl acetate (B) (gradient

Sources & evidence

ORD record
ord-60b2451be580459fb661576ec20010ac
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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