Hydrochloric Acid → HCID 21963919, compound

HRID 2212369Notes

Reaction equation

HRID 2212369 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([S:7]([CH2:10][CH:11]1[CH2:16][CH2:15][C:14]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH2:13][CH2:12]1)(=[O:9])=[O:8])[CH3:6])C.[OH-].[Li+].Cl>CO.O>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([S:25]([C:14]2([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])[CH2:13][CH2:12][CH:11]([CH2:10][S:7]([CH:5]([CH3:6])[C:4]([OH:35])=[O:3])(=[O:9])=[O:8])[CH2:16][CH2:15]2)(=[O:26])=[O:27])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21048987HCID 21048987, compound

Product 1

HCID 21963919HCID 21963919, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Example 73 (55 mg, 0.1 mmol) was dissolved in methanol (2 mL) and lithium hydroxide (12 mg, 0.5 mmol) added. The reaction was stirred at room temperature overnight, diluted with water, acidified with 2M aqueous hydrochloric acid solution and extracted with ethyl acetate (x3). The organic extracts were washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica eluting with ethyl acetate to give a white solid (48 mg).

Workup

  1. extractionextracted with ethyl acetate (x3)
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-d1bf32176b464e229dc072bed7e945a8
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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