4-Toluenesulfonyl chloride → HCID 86591977, compound

HRID 1372801Notes

Reaction equation

HRID 1372801 reaction equation
[OH:1][C@@H:2]1[C@@H:9]2[C@@:5]([C:12]([O:14][CH3:15])=[O:13])([O:6][C:7]([CH3:11])([CH3:10])[O:8]2)[O:4][C@@H:3]1[CH2:16][OH:17].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[OH:1][C@@H:2]1[C@@H:9]2[C@@:5]([C:12]([O:14][CH3:15])=[O:13])([O:6][C:7]([CH3:11])([CH3:10])[O:8]2)[O:4][C@@H:3]1[CH2:16][O:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 90786985HCID 90786985, compound

Product 1

HCID 86591977HCID 86591977, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 11 (1.0 g, 4.0 mmol) in pyridine (13 mL, Aldrich) at 0° C. (ice water bath) was added TsCl (0.76 g, 4.0 mmol, Aldrich) in portions. The resulting mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc/H2O. The EtOAc layer was washed with H2O (2×40 mL), brine (1×40 mL) and dried over MgSO4. EtOAc was evaporated and the crude material was purified by silica gel chromatography using EtOAc/Hexane. Product 17 was obtained as a white solid (1.0 g; yield 63%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc/H2O
  3. washThe EtOAc layer was washed with H2O (2×40 mL), brine (1×40 mL)
  4. dry with materialdried over MgSO4
  5. customEtOAc was evaporated
  6. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-343b68cb469249bfaa51a561dc1b5e7f
Source dataset
uspto-grants-2007_01
Patent number
US07160535B2

Reaction notes

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