Hydrochloric Acid → HCID 58026180, compound

HRID 2387322Notes

Reaction equation

HRID 2387322 reaction equation
[CH3:1][C:2]([C:21]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:22]=1[C:23]([NH2:25])=[O:24])([CH3:20])[CH2:3][C@:4]([O:12][Si](CC)(CC)CC)([C:8]([F:11])([F:10])[F:9])[CH2:5][C:6]#[CH:7].Cl>CO>[F:30][C:27]1[CH:28]=[CH:29][C:21]([C:2]([CH3:20])([CH3:1])[CH2:3][C@:4]([OH:12])([C:8]([F:10])([F:11])[F:9])[CH2:5][C:6]#[CH:7])=[C:22]([CH:26]=1)[C:23]([NH2:25])=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58026166HCID 58026166, compound

Product 1

HCID 58026180HCID 58026180, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.1 g of 2-((S)-1,1-dimethyl-3-triethylsilanyloxy-3-trifluoromethylhex-5-ynyl)-5-fluorobenzamide (15.7 mmol) in 80 mL of MeOH was added 400 mL of HCl (4 N in dioxane, 1.6 mol). The reaction was stirred for 2 hours at room temperature. The volatiles were concentrated in vacuo and 500 mL of water was added. The reaction mixture was then extracted with ethyl acetate, dried over sodium sulfate, and concentrated in vacuo to afford 5.2 g (100%) of 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzamide.

Workup

  1. concentrationThe volatiles were concentrated in vacuo and 500 mL of water
  2. additionwas added
  3. extractionThe reaction mixture was then extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-addd1e270f394be7b4f169fe780dd79b
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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