Hydrochloric Acid → HCID 22010142, compound

HRID 322906Notes

Reaction equation

HRID 322906 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)=[CH:28][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[C:16]([O:18]COCC[Si](C)(C)C)[CH:15]=[CH:14][C:13]=1[CH3:27])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2].Cl>O1CCCC1>[C:1]([C:3]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)=[CH:28][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=1[CH3:27])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22010506HCID 22010506, compound

Product 1

HCID 22010142HCID 22010142, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (RS)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2-methyl-5-(2-(trimethylsilyl)ethoxymethoxy)phenyl)butanoic acid (1.8 g) in tetrahydrofuran (150 mL) is treated with 1 N hydrochloric acid (10 mL) and the mixture heated at reflux for 1 hour. The reaction mixture is evaporated and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The organic phase is washed with water (100 mL), brine (100 mL), dried over magnesium sulphate and evaporated. The residual brown gum (1.25 g) is recrystallised from acetonitrile to give (RS)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(5-hydroxy-2-methylphenyl)butanoic acid (0.5 g) as a cream solid, m.p. 198-200° C. [Elemental analysis:- C,68.32; H,5.45; N,6.93%. Calculated:- C,68.89; H,5.30; N,6.69%]

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. customThe reaction mixture is evaporated
  4. customthe residue partitioned between ethyl acetate (200 mL) and water (100 mL)
  5. washThe organic phase is washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residual brown gum (1.25 g) is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-0fcc8aa92fe4449288fd1970570314c0
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…