Hydrochloric Acid → HCID 22010157, compound

HRID 322903Notes

Reaction equation

HRID 322903 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[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])#[N:2].[OH-].[Na+].Cl>CO>[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[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53853519HCID 53853519, compound

Product 1

HCID 22010157HCID 22010157, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2,5-dimethylphenyl)butanoate (500 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 (20 mL) and extracted three times 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 brown oil. Crystallisation with cyclohexane gives (RS)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)-4-(2,5-dimethylphenyl) butanoic acid, (170 mg) in the form of an off-white solid, m.p. 135-136° C. [Elemental analysis:- C,68.4, H, 5.46, N, 3.33%. Calculated:- C,68.7, H, 5.57, N, 3.00%]

Workup

  1. extractionextracted three times 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 brown oil
  7. customCrystallisation with cyclohexane

Sources & evidence

ORD record
ord-ab089bd6db09404da5237e326f867a10
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…