Water → HCID 53319918, compound

HRID 2042946Notes

Reaction equation

HRID 2042946 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.[F-:40].[K+].O>C(O)CO>[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][F: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 522689Potassium FluorideHCID 86680891HCID 86680891, compound

Product 1

HCID 53319918HCID 53319918, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

The solution of toluenesulfonate 90 (200 mg, 0.34 mmol) and potassium fluoride (23.5 mg 0.41 mmol) in ethylene glycol (3.5 mL) was stirred at 100° C. for 20 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 94 (16 mg, 11%) as a solid.

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-14fbf5d524e3420e82e636ec4803322d
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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