Sodium Chloride → HCID 11667157, compound

HRID 910826Notes

Reaction equation

HRID 910826 reaction equation
[Cl-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][C:9]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:10]=1[CH2:11][CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])#[N:4]>CS(C)=O.O>[C:3]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][C:9]1[CH:26]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:24]=[CH:23][C:10]=1[CH2:11][CH2:12][C:13]([OH:15])=[O:14])#[N:4]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 67390629HCID 67390629, compound

Product 1

HCID 11667157HCID 11667157, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Sodium chloride (0.1 g) was added to a solution of the product from step (iv) (0.6 g) in DMSO (5 ml) and water (1 ml) then heated at 120° C. for 12 hours. The mixture was cooled and partitioned between 2M sodium hydroxide and diethylether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate and the organic layer dried and evaporated under reduced pressure. The residue was purified by reverse phase HPLC. Yield 0.108 g.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 2M sodium hydroxide and diethylether
  3. extractionextracted with ethyl acetate
  4. customthe organic layer dried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-6d4158f427254146bedf52bbb9aad8a7
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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