Hydrochloric Acid → HCID 22010185, compound

HRID 322908Notes

Reaction equation

HRID 322908 reaction equation
[C:1]([C:3]1[C:24]([F:25])=[CH:23][C:22]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:21][C:4]=1[O:5][CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])#[N:2].[OH-].[Na+].Cl>CO>[C:1]([C:3]1[C:24]([F:25])=[CH:23][C:22]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:21][C:4]=1[O:5][CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54541796HCID 54541796, compound

Product 1

HCID 22010185HCID 22010185, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-(2-cyano-3-fluoro-5-(3-thienylmethoxy)phenoxy)-4-(2-methylphenyl)butanoate (200 mg) in methanol (20 mL) containing 1 N sodium hydroxide (5 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is poured into 0.5 N HCl (30 mL) and extracted three times with ethyl acetate (30 mL). The combined organic phases are washed with brine (20 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a brown oil. Crystallisation with cyclohexane gives (RS)-4-(2-cyano-3-fluoro-5-(3-thienylmethoxy)phenoxy)-4-(2-methylphenyl) butanoic acid, (70 mg) in the form of a white solid, m.p. 150-151° C. [Elemental analysis:- C,64.9, H, 4.74, N, 3.29%. Calculated:- C,64.8, H, 4.81, N, 3.13%]

Workup

  1. extractionextracted three times with ethyl acetate (30 mL)
  2. washThe combined organic phases are washed with brine (20 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto leave a brown oil
  7. customCrystallisation with cyclohexane

Sources & evidence

ORD record
ord-01d8c18c007d4204a6475d10de78e7fd
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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