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Trifluoroacetic acid → [2-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic Acid Methyl Ester

HRID 546921
Notes
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Reaction equation

HRID 546921 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:52])[CH2:12][C:13]1[N:14]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH:37]([O:42][Si](C(C)(C)C)(C)C)[C:38]([CH3:41])([CH3:40])[CH3:39])=[C:31]([CH3:50])[CH:30]=3)([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:20][C:19]=2[CH3:51])[S:16][CH:17]=1)C>ClCCl>[CH3:8][O:10][C:11](=[O:52])[CH2:12][C:13]1[N:14]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:27][CH3:28])([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH:37]([OH:42])[C:38]([CH3:40])([CH3:41])[CH3:39])=[C:31]([CH3:50])[CH:30]=3)[CH2:25][CH3:26])=[CH:20][C:19]=2[CH3:51])[S:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57709067{2-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-thiazol-4-yl}-acetic Acid Ethyl Ester

Product 1

HCID 57443500[2-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic Acid Methyl EsterYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Trifluoroacetic acid (0.15 mL) was added to a solution of {2-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-thiazol-4-yl}-acetic acid ethyl ester (Example 63-(1); 20.7 mg, 0.0318 mmol) in dichloromethane (0.75 mL) at room temperature, and the mixture was stirred at room temperature for one hour and 30 minutes. The solvent in the reaction solution was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to give the title compound (15.9 mg, 93%).

Workup

  1. distillationThe solvent in the reaction solution was distilled off under reduced pressure
  2. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e1264b93a2a244daae5a2e9542c35d4b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes