Triethylamine → HCID 22261981, compound

HRID 1610402Notes

Reaction equation

HRID 1610402 reaction equation
[OH:1][CH:2]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.C([N:47]([CH2:50]C)CC)C>O1CCCC1.O>[C:18]1([CH:2]2[O:1][C:50](=[O:35])[NH:47][CH:3]2[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:12][CH:13]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261879HCID 22261879, compound

Product 1

HCID 22261981HCID 22261981, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-hydroxy-3-(1-naphthalenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (2.64 g, 7.05 mmol) in tetrahydrofuran (50 ml) were added diphenylphosphoryl azide (1.67 ml, 7.76 mmol) and triethylamine (1.5 ml, 10.6 mmol) and the mixture was heated under reflux for 1 hr. The reaction solution was diluted with water (300 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced, pressure. The residue was recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(1-naphthalenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (2.19 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-83bebf87d46e4f4a99810d774a7db5ad
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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