Phenoxy acids for the treatment of neuromuscular disorders
A technology selected from compounds, applied in the field of treatment, prevention and/or improvement of neuromuscular disorders, improvement and/or prevention of neuromuscular disorders, capable of solving problems such as harmful long-term consequences
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Embodiment 1
[1065] Example 1: Synthesis of (S)-2-(4-bromo-2-ethynylphenoxy)propionic acid; synthetic strategy following General Method A
[1066]
[1067] (S)-Methyl 2-(4-bromo-2-iodophenoxy)propionate (1.2)
[1068] To (R)-methyl 2-hydroxypropionate (1.1) (1 mmol), 4-bromo-2-iodophenol (1 mmol) and triphenylphosphine (1.2 mmol) in THF (15 mL) at 0 °C over 20 minutes ) solution was added DIAD (1.2 mmol) dropwise. The solution was stirred for an additional 15 minutes at 0°C. The bright yellow solution was warmed to room temperature and stirred overnight. The volatiles were removed in vacuo to give a dark orange oil. The crude product was purified by silica gel chromatography (0-10% EtOAc / hexanes) to afford (S)-methyl 2-(4-bromo-2-iodophenoxy)propanoate (1.2 ) (75% yield). 1 H NMR (300MHz, CDCl 3 )δ7.91(d,1H); 7.37(dd,1H); 6.58(d,1H); 4.73(q,1H); 3.77(s,3H); 1.70(d,3H); ES-MS:386 [M+1].
[1069] (S)-Methyl 2-(4-bromo-2-ethynylphenoxy)propionate (1.3)
[1070] 1) Methyl (S)-2...
Embodiment 2
[1075] Example 2: Synthesis of (2S)-2-(4-bromo-2-vinylphenoxy)propionic acid; synthetic strategy following General Method A
[1076]
[1077] 4-Bromo-2-vinylphenol (2.2)
[1078] To a solution of sodium hydride (6 mmol) in THF (15 mL) at 0 °C was added methyl-triphenylphosphonium bromide (2 mmol), and the mixture was stirred for 1 h, then 5 in THF was introduced dropwise over 20 min. -Bromo-2-hydroxybenzaldehyde (2.1) (1 mmol). The solution was stirred for an additional 15 minutes at 0°C. The bright yellow solution was warmed to room temperature and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride, and the aqueous solution was extracted with EtOAc (2 x 100 mL). The combined organics were subjected to MgSO 4 Dried and adsorbed onto silica. The crude product was purified by silica gel chromatography (0-10% EtOAc / hexanes) to afford 4-bromo-2-vinylphenol (2.2) (65% yield) as a colorless liquid. 1 H NMR (300MHz, CDCl 3 )δ7.58(d,1H);7...
Embodiment 3
[1084] Example 3: Synthesis of (2S)-2-(4-bromo-2-cyclobutylphenoxy)propionic acid and its sodium salt, following the synthesis strategy of General Method A
[1085]
[1086] 2-(1-Hydroxycyclobutyl)phenol (3.2)
[1087] 2-Bromophenol (3.1) (8.04 mL, 69.4 mmol) was dissolved in dry diethyl ether (144 mL) and cooled to -78°C under nitrogen. N-Butyllithium (2.5M in hexane) (61.0 mL, 153 mmol) was added dropwise, keeping the reaction temperature below -70°C. Once the addition was complete, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature and stirred for 2.5 hours. The reaction mixture was cooled to -78°C, then cyclobutanone (5.18ml, 69.4mmol) was added dropwise while keeping the reaction temperature below -70°C. Once the addition was complete, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched into ice-cold ammonium chloride soluti...
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