3-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl Ester → 3-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid

HRID 1670099Notes

Reaction equation

HRID 1670099 reaction equation
C([O:5][C:6](=[O:48])[C:7]1[CH:12]=[C:11]([C:13]2[C:17]([CH3:18])=[CH:16][S:15][CH:14]=2)[CH:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]=2[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:8]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH2:46]([O:45][C:43]([CH2:42][CH2:41][C:27]1[C:28]([O:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([C:13]2[C:17]([CH3:18])=[CH:16][S:15][CH:14]=2)[CH:10]=1)[C:6]([OH:48])=[O:5])=[O:44])[CH3:47]

Participants

4

Reactant 1

HCID 673389343-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl Ester

Product 1

HCID 673382323-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic AcidYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic acid tert-butyl ester (1.8 g) was dissolved in a mixture of TFA and dichloromethane (1:1, 20 mL) and stirred at room temperature for 1 h. The solvents were removed under reduced pressure and the crude material was purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (1.2 g, 73% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-cd9a77b6740d4a5886e648e712576022
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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