Hydrochloric Acid → HCID 22010137, compound

HRID 322901Notes

Reaction equation

HRID 322901 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:4]=1[O:5][CH:6]([C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])#[N:2].[OH-].[Na+].Cl>CO>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[CH:6]([O:5][C:4]1[CH:22]=[C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH:24]=[CH:25][C:3]=1[C:1]#[N:2])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53775193HCID 53775193, compound

Product 1

HCID 22010137HCID 22010137, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2-chloro-6-fluorophenyl)butanoate (360 mg) in methanol (10 mL) containing 1 N sodium hydroxide (3 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is poured into 0.5 N HCl (20 mL) and extracted twice with ethyl acetate (20 mL). The combined organic phases are washed with brine (20 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a dark yellow oil. Crystallisation from a mixture of cyclohexane and ethyl acetate gives (RS)-4-(2-chloro-6-fluorophenyl)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-butanoic acid (210 mg) in the form of a beige solid, m.p. 128-130° C.

Workup

  1. extractionextracted twice with ethyl acetate (20 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 dark yellow oil
  7. customCrystallisation
  8. additionfrom a mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-26744bcc565e452db3dc79c9f745de38
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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