4-Toluenesulfonyl chloride → HCID 58743810, compound

HRID 2112310Notes

Reaction equation

HRID 2112310 reaction equation
[OH:1][C@@H:2]1[CH2:26][C@@H:25]2[C@:20]([CH3:31])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][OH:30])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:33])([C@@H:17]([OH:32])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1.[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>[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:31])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][O:30][S:40]([C:37]3[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=3)(=[O:42])=[O:41])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:33])([C@@H:17]([OH:32])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 90828874HCID 90828874, 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% HCI 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% HCI 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-517593df64ea4e6a85f9250a293b21be
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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