2-Methoxyethanol → HCID 86622893, compound

HRID 1891414Notes

Reaction equation

HRID 1891414 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([CH3:62])=[C:44]([CH:61]=1)[CH2:45][NH:46][C:47]([C:49]1[O:53][N:52]=[C:51]([NH:54][C:55](=[O:60])[C:56]([F:59])([F:58])[F:57])[CH:50]=1)=[O:48]>C1COCC1>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([CH3:62])=[C:44]([CH:61]=1)[CH2:45][NH:46][C:47]([C:49]1[O:53][N:52]=[C:51]([N:54]([CH2:4][CH2:3][O:2][CH3:1])[C:55](=[O:60])[C:56]([F:58])([F:59])[F:57])[CH:50]=1)=[O:48]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59799402HCID 59799402, compound

Product 1

HCID 86622893HCID 86622893, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a round bottom flask was placed 2-methoxyethanol (89.1 μL, 1.13 mmol), and triphenylphosphine (0.296 g, 1.13 mmol) under an atmosphere of nitrogen in THF (4.7 mL). The solution was cooled to 0° C. and diisopropyl azodicarboxylate (0.238 mL, 1.21 mmol) was added dropwise. After stirring for 15 min, N-(5-chloro-2-methylbenzyl)-3-[(trifluoroacetyl)amino]isoxazole-5-carboxamide (0.292 g, 0.807 mmol) in THF (4.7 mL) was added to reaction flask. The ice bath was removed and the resulting solution was stirred at rt for 15 h. The reaction solution was diluted with 1 N HCl and ethyl acetate. The aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (30% ethyl acetate/hexs) to give the desired product as a white solid (300 mg, 89%). LCMS calculated for C17H18ClF3N3O4(M+H)+: m/z=420.1.

Workup

  1. customInto a round bottom flask was placed
  2. customThe ice bath was removed
  3. stirringthe resulting solution was stirred at rt for 15 h
  4. additionThe reaction solution was diluted with 1 N HCl and ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate once
  6. washThe combined organic solutions were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (30% ethyl acetate/hexs)

Sources & evidence

ORD record
ord-e0b4575ba27b4b9999f50947ce13be63
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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