4-Toluenesulfonyl chloride → HCID 86659055, compound

HRID 2407678Notes

Reaction equation

HRID 2407678 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[C:19]1([C:25]2[CH:29]=[C:28]([CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([CH2:37][OH:38])[CH2:33][CH2:32]3)[O:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:38][CH2:37][CH:34]2[CH2:33][CH2:32][N:31]([CH2:30][C:28]3[O:27][N:26]=[C:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:29]=3)[CH2:36][CH2:35]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 52234807HCID 52234807, compound

Product 1

HCID 86659055HCID 86659055, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (12.1 mL) and p-toluene sulfonylchloride (6.61 g) were added sequentially to a room temperature mixture of the compound prepared in Example 64 (7.86 g) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed sequentially with a saturated aqueous sodium bicarbonate solution and brine. The combined organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to obtain the title compound (1.52 g) having the following physical data.

Workup

  1. washwashed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-96c5c674ca754ab3beeab4481d0c4685
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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