Hydrochloric Acid → 2-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

HRID 62910Notes

Reaction equation

HRID 62910 reaction equation
[Li+].[OH-].OO.C([C@@H]1COC(=O)N1[C:18]([CH:20]1[CH2:22][CH:21]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=1)=[O:19])C1C=CC=CC=1.[O-:32]S([O-])=O.[Na+].[Na+].Cl>O.C1COCC1.O>[F:31][C:25]1[CH:24]=[C:23]([CH:21]2[CH2:22][CH:20]2[C:18]([OH:19])=[O:32])[CH:28]=[CH:27][C:26]=1[O:29][CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 90118203(R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

Product 1

HCID 211905602-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

After LiOH (0.059 g, 1.40 mmol) was dissolved in water (5 mL), H2O2 (0.3 mL, 3.52 mmol) was added thereto, and the mixture was stirred at room temperature for 30 minutes. The reactant was added to the solution of (R)-4-benzyl-3-[2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-o n (0.325 g, 0.88 mmol) obtained in Step C of Preparation Example 61 in THF/H2O (17 mL/4.4 mL) at 0° C., and the mixture was stirred for 1 hour. After the termination of the reaction, Na2SO3 (1 g) dissolved in water (5 mL) was added thereto, and the mixture was stirred at 0° C. for 1 hour. 6N HCl was added thereto to adjust the pH to 2, and the reactant was extracted with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound, which was used in the next step without a separate purification process

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. additionwas added
  3. stirringthe mixture was stirred at 0° C. for 1 hour
  4. extractionthe reactant was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-742d23f7f38b455b879dbb8ad7677fce
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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