(4-{3-[3-Bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester → (4-{3-[3-Bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid

HRID 548555Notes

Reaction equation

HRID 548555 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:19]=[C:18]([Br:31])[CH:17]=2)=[CH:8][C:7]=1[CH3:32]>C(O)C.[OH-].[Na+]>[Br:31][C:18]1[CH:17]=[C:16]([C:15]#[C:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[C:7]([CH3:32])[CH:8]=2)[CH:21]=[C:20]([C:22]#[C:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH:19]=1

Participants

4

Reactant 1

HCID 67157959(4-{3-[3-Bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester

Product 1

HCID 24752597(4-{3-[3-Bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (4-{3-[3-bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (45 mg, 0.088 mmol) in ethanol (5 ml) and 1N NaOH (0.5 ml) was stirred at 75° C. for 30 min. The reaction mixture was evaporated and the residue dissolved in water (2 ml). Aqueous 1N HCl (0.5 ml) was added and the mixture was extracted with methylene chloride (3×15 ml). The combined organic phases were dried and evaporated to give the title compound in 36 mg (88%) yield.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in water (2 ml)
  3. additionAqueous 1N HCl (0.5 ml) was added
  4. extractionthe mixture was extracted with methylene chloride (3×15 ml)
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-9bd90eb3280246de8eead5b208097b50
Source dataset
uspto-grants-2011_05
Patent number
US07943612B2

Reaction notes

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