Trifluoroacetic acid → 3-(3-(1-Ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid

HRID 909892Notes

Reaction equation

[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[N:5]=[N:4]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:5]=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl 3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate [Example 4, Step iii)] (382 mg), DCM (5 mL) and TFA (5 mL) was stirred at 25° C. for 30 min and concentrated under vacuum to give the subtitled compound as a gum (625 mg). 1H NMR (300 MHz, CDCl3) δ 7.92 (s, 1H), 7.75 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.37 (t, J=7.6 Hz, 1H), 7.24 (s, 1H), 4.53 (q, J=7.4 Hz, 2H), 3.76 (t, J=5.9 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H), 2.93 (t, J=6.0 Hz, 2H), 2.63 (t, J=5.9 Hz, 2H), 1.67 (t, J=7.4 Hz, 3H).

Workup

concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-c653848e0a704ad59f685705e83a7b4d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017602B2

Reaction notes

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