4-Toluenesulfonyl chloride → HCID 67904964, compound

HRID 465640Notes

Reaction equation

HRID 465640 reaction equation
[CH2:1]([NH:19][CH2:20][C:21]([NH:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=1[O:34][CH3:35])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][CH:44]=1.[K+].[Br-]>C(OCC)(=O)C>[CH3:53][C:43]1[CH:48]=[CH:47][C:46]([S:49]([N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:20][C:21]([NH:23][C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])=[O:22])(=[O:51])=[O:50])=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 253877Potassium BromideHCID 67904675HCID 67904675, compound

Product 1

HCID 67904964HCID 67904964, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.50 g of the product of Example 7, excess triethylamine, and ethyl acetate at room temperature was added 0.25 g p-toluene sulfonyl chloride and this was allowed to sit 3 days at room temperature. The reaction mixture was then washed with H3PO4, NaHCO3, and NaCl solutions, dried over MgSO4, filtered, and stripped to an oil. This oil was purified by chromatography on silica gel (70-230 mesh) using 1/1 hexane/EtoAc as eluant. The product was obtained as a viscous oil. 0.28 g (42%). NMR (CDCl3) δ 0.88 (3H, z), δ 1.26 (24H, m), δ 1.66 (2H, m), δ 2.01 (4H, m), δ 2.44 (3H, s), δ 3.21 (2H, m), δ 3.79-3.88 (9H, m), δ 5.34 (2H, m), δ 6.15 (2H, s), δ 7.26-7.75 (5H, m). IR (KBr) 3019, 2925, 1599, 1466, 1206 cm-1.

Workup

  1. washThe reaction mixture was then washed with H3PO4, NaHCO3, and NaCl solutions
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThis oil was purified by chromatography on silica gel (70-230 mesh)
  5. customThe product was obtained as a viscous oil

Sources & evidence

ORD record
ord-74b0f04d32ad4d4ca01c704fafbaa841
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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