Hydrochloric Acid → HCID 178461994, compound

HRID 46143Notes

Reaction equation

HRID 46143 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)([CH3:17])[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:4][CH:3]=1.O.O.[OH-].[Li+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=3)([CH3:17])[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178497560HCID 178497560, compound

Product 1

HCID 178461994HCID 178461994, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-((S)-1-(4-fluorophenyl)ethylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)benzoate (0.64 g, 1.7 mmol) in THF (3 mL), MeOH (1 mL), and H2O (1 mL) was added lithium hydroxide monohydrate (0.10 g, 2.5 mmol), and the mixture was stirred at ambient temp. overnight. The mixture was then heated to reflux for 5 h. The mixture was neutralized with 1N HCl, and then extracted with CH2Cl2 five times. The organic extracts were dried over Na2SO4, concentrated in vacuo, and the product was dried on vacuum. MS: 373 (M+1).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 5 h
  3. extractionextracted with CH2Cl2 five times
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe product was dried on vacuum

Sources & evidence

ORD record
ord-ba1a04af585243edb172ed6eff5e70af
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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