Triphenylphosphine → Ethyl [2-methyl-4-({[4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl}-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)phenoxy]acetate

HRID 270154Notes

Reaction equation

HRID 270154 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:6][C:7]=1[CH2:8][S:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:23])[CH:11]=1.[CH3:34][C:35]1[O:39][N:38]=[C:37]([C:40]2[CH:41]=[C:42](O)[CH:43]=[CH:44][CH:45]=2)[N:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:23][C:12]1[CH:11]=[C:10]([S:9][CH2:8][C:7]2[S:6][C:5]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=3)=[N:4][C:3]=2[CH2:2][O:1][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([C:37]3[N:36]=[C:35]([CH3:34])[O:39][N:38]=3)[CH:41]=2)[CH:22]=[CH:21][C:13]=1[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 120425193-(5-Methyl-1,2,4-oxadiazol-3-yl)phenolHCID 86591789Ethyl [4-({[4-(hydroxymethyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-2-methylphenoxy]acetate

Product 1

HCID 86591788Ethyl [2-methyl-4-({[4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl}-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)phenoxy]acetateYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of ethyl [4-({[4-(hydroxymethyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-2-methylphenoxy]acetate (40mg, 0.08mmoles, 1eq) in dry toluene (2ml) was added 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol (15mg, 0.088mmoles, 1.1eq) followed by triphenylphosphine (25mg, 0.096mmoles, 1.2eq) as a solid. Diisopropylazodicarboxylate (0.017ml, 0.088mmoles, 1.1eq) was then added dropwise and the reaction was stirred for 2hours at room temperature. The reaction was then partitioned between EtOAc and H2O. After the separation of the phases the organic phase washed with 0.1N NaOH, brine, dried over Na2SO4, filtered, concentrated in vacuo and purified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes) to yield 40mg (76%) of product.

Workup

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. customAfter the separation of the phases the organic phase
  3. washwashed with 0.1N NaOH, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-3a08f893d6314f1dba3850155675d862
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Reaction notes

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