Trifluoroacetic acid → HCID 57708983, compound

HRID 547112Notes

Reaction equation

HRID 547112 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:53])[CH2:11][C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]([O:43][Si](C(C)(C)C)(C)C)[C:39]([CH3:42])([CH3:41])[CH3:40])=[C:32]([CH3:51])[CH:31]=3)([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:21][C:20]=2[CH3:52])[CH:15]=[C:16]([OH:18])[CH:17]=1>ClCCl>[CH3:8][O:9][C:10](=[O:53])[CH2:11][C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH2:28][CH3:29])([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]([OH:43])[C:39]([CH3:41])([CH3:42])[CH3:40])=[C:32]([CH3:51])[CH:31]=3)[CH2:26][CH3:27])=[CH:21][C:20]=2[CH3:52])[CH:15]=[C:16]([OH:18])[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57708963HCID 57708963, compound

Product 1

HCID 57708983HCID 57708983, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.12 mL) was added to a solution of [4′-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-5-hydroxy-2′-methyl-biphenyl-3-yl]-acetic acid methyl ester (Example 165-(2); 15.9 mg, 0.0247 mmol) in dichloromethane (0.60 mL) at room temperature, and the mixture was stirred at room temperature for one hour. The solvent in the reaction solution was distilled off under reduced pressure, and the residue was diluted with diethyl ether. The mixture was adjusted to pH 7 with aqueous sodium bicarbonate solution, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1) to give the title compound (11.5 mg, 88%).

Workup

  1. distillationThe solvent in the reaction solution was distilled off under reduced pressure
  2. additionthe residue was diluted with diethyl ether
  3. extractionfollowed by extraction with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ab86d82bf7b345ed89fce374c1d58de4
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…