Hydrochloric Acid → HCID 23204195, compound

HRID 322915Notes

Reaction equation

HRID 322915 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:21][C:5]=1[O:6][CH:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]#[N:20])[C:8]([O-:10])=[O:9])(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:4]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:21][C:5]=1[O:6][CH:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]#[N:20])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131722483HCID 131722483, compound

Product 1

HCID 23204195HCID 23204195, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-[(2-acetyl-5-(3-thienylmethoxy)-phenoxy]-4-(2-cyanophenyl)butanoate (250 mg) in methanol (10 ml) containing 1N sodium hydroxide (3 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is poured into 0.5 N hydrochloric acid (20 mL) and extracted twice with ethyl acetate (20 mL). The combined organic phases are washed with brine (20 mL), dried over magnesium sulphate and concentrated under reduced pressure to leave a dark yellow oil. Crystallization from a mixture of cyclohexane and ethyl acetate affords (RS)-4-[(2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-cyanophenyl)butanoic acid (20 mg) in the form of a beige solid, m.p. 132-134° C. [Elemental analysis:- C, 66.0, H, 4.87, N, 3.02%. Calculated:- C, 66.2, H, 4.86, N, 3.22%].

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. concentrationconcentrated under reduced pressure
  5. customto leave a dark yellow oil
  6. customCrystallization
  7. additionfrom a mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-6f00789a96d047f495d58a9e935b9006
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…