1,4-Dioxane → {3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid

HRID 885245Notes

Reaction equation

HRID 885245 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1.C(N(C(C)C)CC)(C)C.[O:36]1CCOC[CH2:37]1>>[O:36]=[C:37]1[N:4]([CH2:5][C:6]2[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:7]=2[O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2][O:1]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 58237504(3-{2-[(2-Hydroxy-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acid

Product 1

HCID 44187532{3-[2-(2-Oxo-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid

Conditions

Temperature
70 °C

Procedure

(3-{2-[(2-Hydroxy-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acid (0.15 g, 0.41 mmol), N,N′-carbonyldiimidazole (0.1 g, 0.61 mmol), and diisopropylethylamine (1 mL) were combined in 1,4-dioxane (5 mL) and stirred at 70° C. for 2 hours. The mixture was concentrated and purified by preparative HPLC to give the desired product (0.01 g).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2c9ce30036bc4b6588a312a8f67e5fab
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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