[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl Ester → (4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-acetic Acid

HRID 546930Notes

Reaction equation

HRID 546930 reaction equation
C[O:2][C:3](=[O:45])[CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]([O:35][Si](C(C)(C)C)(C)C)[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:24]([CH3:43])[CH:23]=3)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=2[CH3:44])[CH:8]=[CH:9][CH:10]=1>ClCCl.FC(F)(F)C(O)=O>[CH2:18]([C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:45])=[O:2])[CH:6]=2)=[C:12]([CH3:44])[CH:13]=1)([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]([OH:35])[C:31]([CH3:33])([CH3:34])[CH3:32])=[C:24]([CH3:43])[CH:23]=1)[CH2:20][CH3:21])[CH3:19]

Participants

3

Reactant 1

HCID 57708909[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl Ester

Product 1

HCID 15941706(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-acetic AcidYield 80.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

[4′-(1-{4-[3-(t-Butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2′-methyl-biphenyl-3-yl]-acetic acid methyl ester (Example 66-(1); 36 mg, 0.057 mmol) was dissolved in dichloromethane/trifluoroacetic acid=1/5 (1 mL), and the solution was stirred at room temperature for three hours. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1). The product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL). A 1 N sodium hydroxide aqueous solution (0.1 mL) was added, and the mixture was stirred at room temperature for one hour. A 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give the title compound (23 mg, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1)
  3. dissolutionThe product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL)
  4. additionA 1 N sodium hydroxide aqueous solution (0.1 mL) was added
  5. stirringthe mixture was stirred at room temperature for one hour
  6. additionA 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-18c493705eb847aa88898b24e78fa12f
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…