Water → HCID 86680891, compound

HRID 2042943Notes

Reaction equation

HRID 2042943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[CH:23][N:24]=1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.O>N1C(C)=CC=CC=1C>[CH3:40][C:30]1[CH:35]=[CH:34][C:33]([S:36]([O:18][CH2:17][C@@H:10]2[C@@H:11]([OH:16])[C@H:12]([OH:15])[C@@H:13]([OH:14])[C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:19][C:20]4[S:21][C:22]([C:25]5[O:26][CH:27]=[CH:28][CH:29]=5)=[CH:23][N:24]=4)[CH:4]=3)[O:9]2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 51003384HCID 51003384, compound

Product 1

HCID 86680891HCID 86680891, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Procedure

The solution of alcohol 89 (1.0 g, 2.28 mmol) and p-toluenesulfonyl chloride (2.3 g, 11.8 mmol) in 2,6-lutidine (22.8 mL) was stirred at room temperature for 15 h. H2O (150 mL) was added to the reaction mixture and then extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel column chromatography provided desired toluenesulfonate 90 (1.03 g, 78%) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-efa3d9edf6014d4e921bd0d800aa4d31
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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