Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate → 3-(4-((2'-(Hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoic acid

HRID 2422307Notes

Reaction equation

HRID 2422307 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:19][CH:18]=2)[CH:10]=1>FC(F)(F)C(O)=O>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

Participants

3

Reactant 1

HCID 23082953Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate

Product 1

HCID 230831773-(4-((2'-(Hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoic acidYield 5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-(4-((2′-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate (0.25 g, 0.60 mmol) was dissolved in trifluoroacetic acid (2 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was purified by preparative HPLC (gradient cycle A) to give the title compound (10 mg, 5%) as colorless crystals. MS (APCI−): 361 (M−H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative HPLC (gradient cycle A)

Sources & evidence

ORD record
ord-98873aa7664040c5af391453c55a4ccf
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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