Hydrochloric Acid → HCID 21963958, compound

HRID 2212368Notes

Reaction equation

HRID 2212368 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][S:6][CH2:7][CH:8]1[CH2:13][CH2:12][C:11]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[CH2:10][CH2:9]1)C.[OH-].[Li+].Cl>CO.O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([C:11]2([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])[CH2:10][CH2:9][CH:8]([CH2:7][S:6][CH2:5][C:4]([OH:32])=[O:3])[CH2:13][CH2:12]2)(=[O:24])=[O:23])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21048988HCID 21048988, compound

Product 1

HCID 21963958HCID 21963958, compoundYield 772%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Example 69 (15 mg, 0.003 mmol) was dissolved in methanol (1 mL) and lithium hydroxide (1 mg, 0.015 mmol) added. The reaction was stirred at room temperature overnight, diluted with water, acidified with 2 M aqueous hydrochloric acid 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 iso-hexane/ethyl acetate (1:1) to give a white solid (11 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 iso-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-98bb819b91224c4fbf4f55116963efec
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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