Trifluoroacetic acid → 3-[(2-Carbomethoxyethyl)thio]-3-[2-(8-phenyloctyl)phenyl]propanoic acid

A solution of t-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoate (4.0 gm, 9.7 mmole) in methylene chloride (40 ml) was stirred under an inert atmosphere at -10° C. To this cold solution was added methyl 3-mercaptopropionate (6.2 ml, 56 mmole) in one portion followed by dropwise addition of trifluoroacetic acid (80 ml). The reaction mixture was then stirred for 5 hours at 0° C. Solvent and excess trifluoroacetic acid were removed on a rotary evaporator. The residue was redissolved in methylene chloride and washed twice with water and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography on silica gel eluting with hexane-ethyl acetate-formic acid (85/15/0.5) gave the title compound. Anal.: Calcd. for C27H36O4S: C, 71.17; H, 7.74. Found: C, 70.46; H, 7.72. 250 MHz NMR (CDCl3) δ1.28-1.68 (12 H,m) 2.48 (2 H,t) 2.56-2.72 (6 H,m) 2.93 (2 H,d) 3.66 (3 H,s) 4.60 (1 H,t) 7.18-7.39 (9 H,m).

1. customSolvent and excess trifluoroacetic acid were removed on a rotary evaporator
2. dissolutionThe residue was redissolved in methylene chloride
3. washwashed twice with water and once with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customevaporated

ORD record

ord-4c7dc5ae8dc94dcb85bf23e1e83b10ce

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05189226