1,4-Dioxane → {3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid

HRID 885361Notes

Reaction equation

[OH:1][C@H:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:3]([NH:5][CH2:6][C:7]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:8]=1[O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1)[CH3:4].C(N(C(C)C)CC)(C)C.[O:43]1CCOC[CH2:44]1>>[CH3:4][C@H:3]1[C@@H:2]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:1][C:44](=[O:43])[N:5]1[CH2:6][C:7]1[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:8]=1[O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 312751,4-Dioxane

HCID 81531Diisopropylethylamine

HCID 58237447(3-{2-[((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acid

Product 1

HCID 44187170{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid

Conditions

Temperature: 80 °C

Procedure

(3-{2-[((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethylamino)-methyl]-4-trifluoromethyl-phenoxy}-phenyl)-acetic acid (0.15 g, 0.33 mmol), N,N′-carbonyldiimidazole (0.065 g, 0.4 mmol), and diisopropylethylamine (1 mL) were combined in 1,4-dioxane (5 mL) and stirred at 80° C. overnight. After work-up, the crude material was purified by preparative HPLC to give the desired product (0.04 g).

Workup

customAfter work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-be149f786bd94b64b99bb42af41614ef
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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