Water → HCID 86680892, compound

HRID 2042947Notes

Reaction equation

HRID 2042947 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([OH:21])[C@H:15]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][C:30]4[S:31][C:32]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)=[CH:33][N:34]=4)[CH:23]=3)[O:14]2)(=O)=O)=CC=1.[I-:40].[Na+].O>CC(=O)CC>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C@H:15]2[C@H:16]([OH:21])[C@@H:17]([OH:20])[C@H:18]([OH:19])[C@@H:13]([CH2:12][I:40])[O:14]2)=[CH:23][C:24]=1[CH2:29][C:30]1[S:31][C:32]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)=[CH:33][N:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 86680891HCID 86680891, compound

Product 1

HCID 86680892HCID 86680892, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The solution of toluenesulfonate 90 (100 mg, 0.17 mmol) and sodium iodide (38 mg 0.25 mmol) in 2-butanone (1.7 mL) was stirred at 80° C. for 2 h. H2O was added to the reaction mixture and then extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by prep HPLC (C18) to afford the titled compound 95 (45 mg, 48%) as a solid. MH+547

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-89da5fa6d5d14483b7585876944b1f34
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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