1-Methylimidazole → 4-(1-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-yloxy)-4-oxobutanoic acid triethylamine salt

1-(bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-ol (6.8 g, 11.0 mmoles), succinic anhydride (1.1 g, 11.0 mmoles), triethylamine (4.6 mL, 33.0 mmoles) and 1-methylimidazole (0.44 mL, 5.5 mmoles) are dissolved in methylene chloride (68 mL). The reaction is stirred at ambient temperature for five days, during which time the solution darkened. The solution is then diluted with methylene chloride (100 mL) and washed twice with ice-cold aqueous citric acid (10% [w/v], 50 mL) and once with saturated aqueous sodium chloride (50 mL). The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and evaporated to a dark resin. The crude product is purified on silica gel (200 mL bed volume) eluting with methylene chloride:triethylamine (95:5 [v/v/v], 500 mL), then methylene chloride:methanol:triethylamine (93:2:5 [v/v/v], 1000 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to a resin. The resin is dried well in vacuo. The yield is 2.4 g (30%).

1. washwashed twice with ice-cold aqueous citric acid (10% [w/v], 50 mL) and once with saturated aqueous sodium chloride (50 mL)
2. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
3. filtrationfiltered
4. customevaporated to a dark resin
5. customThe crude product is purified on silica gel (200 mL bed volume)
6. washeluting with methylene chloride:triethylamine (95:5 [v/v/v], 500 mL)
7. additionFractions containing pure product by thin layer chromatography
8. customevaporated to a resin
9. customThe resin is dried well in vacuo

ORD-Eintrag

ord-ddd8ad3cc9354c3692719c4d2c851518

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08501706B2