3'-[4-(2-Tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid → 3'-((4-(2-Carboxyethyl)phenoxy)methyl)biphenyl-2-carboxylic acid

HRID 2422301Notes

Reaction equation

HRID 2422301 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:6]([CH2:8][CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)([OH:7])=[O:5]

Participants

3

Reactant 1

HCID 575418463'-[4-(2-Tert-butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid

Product 1

HCID 230829923'-((4-(2-Carboxyethyl)phenoxy)methyl)biphenyl-2-carboxylic acidYield 16%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3′-[4-(2-tert-Butoxycarbonylethyl)phenoxymethyl]biphenyl-2-carboxylic acid (0.15 g, 0.35 mmol) was dissolved in trifluoroacetic acid (3 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2-ethyl acetate) to give the title compound (21 mg, yield 16%) as a colorless powder. MS (APCI−): 375 (M−H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2-ethyl acetate)

Sources & evidence

ORD record
ord-6c4e246a7892433cb17c8524daa9b7bf
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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