5-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-3'-fluoro-biphenyl-3-carboxylic acid tert-butyl ester → HCID 67338077, compound

HRID 1670086Notes

Reaction equation

HRID 1670086 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([F:49])[CH:44]=2)[CH:11]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:22]=2[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:13]=1)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH2:41]([O:40][C:38]([CH2:37][CH2:36][C:22]1[C:23]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:12]1[CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[C:10]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([F:49])[CH:44]=2)[CH:11]=1)=[O:39])[CH3:42]

Participants

4

Reactant 1

HCID 673385835-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-3'-fluoro-biphenyl-3-carboxylic acid tert-butyl ester

Product 1

HCID 67338077HCID 67338077, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-3′-fluoro-biphenyl-3-carboxylic acid tert-butyl ester (7.0 g) was dissolved in a mixture of TFA and dichloromethane (1:1, 80 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 (5.9 g, 90% 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-feb875750485446188cfa8897fdd4e3e
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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