4-Toluenesulfonyl chloride → HCID 87983453, compound

HRID 1835872Notes

Reaction equation

HRID 1835872 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][N:18]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH3:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[S:54](Cl)([C:57]1[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=1)(=[O:56])=[O:55]>C(Cl)Cl>[S:54]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:16][CH2:17][N:18]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH3:23])([C:57]1[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=1)(=[O:56])=[O:55]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 23500254HCID 23500254, compound

Product 1

HCID 87983453HCID 87983453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 6.1 g amount of 7,10,13-tri (t-butoxycarbonyl)-7,10,13-triazapentadecanol, 100 mg of dimethylaminopyridine, and 4 ml of triethylamine in 100 ml of CH2Cl2 was stirred at 0° C. Dropwise, 2.64 of tosyl chloride in 20 ml of CH2Cl2 was added at 0° to 5° C. The reaction was then stirred overnight at room temperature and then 100 ml of CH2Cl2 was added. The reaction mixture was washed with 30 ml of 2N HCl, 30 ml of water and 30 ml of brine. The organic layer was dried over MgSO4 and was filtered. The solvent was evaporated and the residue from the filtrate was purified using a silica gel column and eluted with ethyl acetate/hexane (1:2 v/v). About 7.8 g of 7,10,13-tri(t-butoxycarbonyl)-7,10,13-triazapentadecanol tosylate was collected. The reaction is shown below:

Workup

  1. washThe reaction mixture was washed with 30 ml of 2N HCl, 30 ml of water and 30 ml of brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationwas filtered
  4. customThe solvent was evaporated
  5. customthe residue from the filtrate was purified
  6. washeluted with ethyl acetate/hexane (1:2 v/v)
  7. customAbout 7.8 g of 7,10,13-tri(t-butoxycarbonyl)-7,10,13-triazapentadecanol tosylate was collected

Sources & evidence

ORD record
ord-ebde50ef3c824edd91bac94568f4a644
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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