1,2-Dimethoxyethane → HCID 86616209, compound

HRID 426362Notes

Reaction equation

HRID 426362 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([CH:16]([C:21]1[CH:22]=[C:23](OS(C(F)(F)F)(=O)=O)[CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH:26]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:45][C:46]([F:57])([F:56])[C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:15])[CH:16]([C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH:24]=[C:23]([C:50]2[CH:51]=[CH:52][C:47]([C:46]([F:57])([F:56])[F:45])=[CH:48][CH:49]=2)[CH:22]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86616208HCID 86616208, compound

Product 1

HCID 86616209HCID 86616209, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 5-[1-(4-benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-4′-trifluoromethyl-biphenyl-3-yl ester (4.03 g, 6.27 mmol), 4-(trifluoromethyl)phenylboronic acid (1.34 g, 7.05 mmol), 1,2-dimethoxyethane (24 mL) and aqueous Na2CO3 (2 M, 3.2 mL, 6.4 mmol) was stirred while purging N2 at room temperature for 10 min. To this system was added Pd(Ph3)4 (1.45 g, 1.25 mmol) and heated to reflux (95° C.) for 1 h. The red-brown mixture was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 solution (3×50 mL) and brine (2×50 mL). The organic fraction was dried (Na2SO4) and concentrated in vacuo. The crude mixture was purified by ISCO column chromatography to obtain 4-benzyl-3-[2-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-methyl-pentanoyl]-oxazolidin-2-one (3.2 g, 79%).

Workup

  1. customwhile purging N2 at room temperature for 10 min
  2. temperatureheated
  3. washwashed with saturated aqueous NaHCO3 solution (3×50 mL) and brine (2×50 mL)
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by ISCO column chromatography

Sources & evidence

ORD record
ord-91456c9346dc4ec08185043ee04b6727
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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