Hydrochloric Acid → (4-{2-[5-(4-Cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

HRID 9690Notes

Reaction equation

HRID 9690 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[S:11][C:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]45OCC(C)(C[O:31]4)C[O:27]5)=[C:20]([CH3:35])[CH:19]=3)=[C:13]([CH3:15])[CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl>CC(O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]2[S:11][C:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:31])=[O:27])=[C:20]([CH3:35])[CH:19]=3)=[C:13]([CH3:15])[CH:14]=2)=[CH:9][C:2]=1[F:1])#[N:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219863002-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile2×

Product 1

HCID 21986517(4-{2-[5-(4-Cyano-3-fluorophenyl)-3-methylthien-2-yl]ethyl}-2-methylphenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile (intermediate 101, 0.016 g) in 2-propanol (2 ml) was treated with 2M aqueous hydrochloric acid (1 ml) and the mixture stirred at reflux for 2 hours. The solvent was removed and the residue dissolved in 1,4-dioxane (2 ml) and water (1 ml). This mixture was treated with 2M aqueous sodium hydroxide (0.5 ml) and the mixture stirred for 16 hours). The solvent was removed and the residue purified by SPE (aminopropyl). The title compound, as the free acid, was recovered by treating a solution of this product with Dowex H+.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in 1,4-dioxane (2 ml)
  4. additionThis mixture was treated with 2M aqueous sodium hydroxide (0.5 ml)
  5. stirringthe mixture stirred for 16 hours)
  6. customThe solvent was removed
  7. customthe residue purified by SPE (aminopropyl)
  8. customThe title compound, as the free acid, was recovered
  9. additionby treating a solution of this product with Dowex H+

Sources & evidence

ORD record
ord-8b8bdbd070704040b63b19183de9bb48
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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