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

HRID 2108081Notes

Reaction equation

HRID 2108081 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].[SH:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35].FC(F)(F)C(O)=O>C(Cl)Cl>[C:34]([CH2:33][CH2:32][S:31][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][C:4]([OH:6])=[O:5])([O:36][CH3:37])=[O:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18050Methyl 3-mercaptopropionateHCID 15617420Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

Product 1

HCID 150774313-[(2-Carbomethoxyethyl)thio]-3-[2-(8-phenyloctyl)phenyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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 elutinq 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 (12H,m) 2.48 (2H,t) 2.56-2.72 (6 H,m) 2.93 (2H,d) 3.66 (3H,s) 4.60 (1H,t) 7.18-7.39 (9H,m).

Workup

  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

Sources & evidence

ORD record
ord-c8eb2119a00945328b02e758fe894e14
Source dataset
uspto-grants-1990_06
Patent number
US04937253

Reaction notes

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