4-Toluenesulfonyl chloride → HCID 58743810, compound

HRID 724543Notes

Reaction equation

HRID 724543 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][OH:31])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:32])[CH2:10][CH2:9]1)[CH3:7].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][O:31][S:40]([C:37]4[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=4)(=[O:42])=[O:41])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:32])[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 15703127HCID 15703127, compound

Product 1

HCID 58743810HCID 58743810, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

The compound of Example 1B (1.50 g, 3.2 mmol) was dissolved in 15 ml of chloroform and 15 ml of pyridine; p-toluenesulfonyl chloride (920 mg, 4.83 mmol) was added, and the mixture was stirred overnight. Chloroform (250 ml) was added, the resultant solution was washed with 5% HCl solution and sat. Na2SO4. After solvent removal in vacuo, the crude product was purified by column chromatography on silica gel (40%—>60% ethyl acetate/hexanes. The yield of the title compound was 1.40 g (71%).

Workup

  1. washthe resultant solution was washed with 5% HCl solution and sat. Na2SO4
  2. customAfter solvent removal in vacuo
  3. customthe crude product was purified by column chromatography on silica gel (40%—>60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4cda5341c1b24407a87d8b848d0af93d
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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