Water → HCID 178517873, compound

HRID 2362454Notes

Reaction equation

HRID 2362454 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[C@@H:4]([C:21]#[N:22])[O:3]1.Cl.C(N(CC)CC)C.[N-:31]=[N+:32]=[N-:33].[Na+].O>C1(C)C=CC=CC=1>[C:15]1([C:14]#[C:13][C:9]2[CH:8]=[C:7]([C@@H:5]3[C@@H:4]([C:21]4[NH:33][N:32]=[N:31][N:22]=4)[O:3][C:2](=[O:1])[NH:6]3)[CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 69085465HCID 69085465, compound

Product 1

HCID 178517873HCID 178517873, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carbonitrile (35 mg, 0.121 mmol) in Toluene (2 mL) was added triethylamine hydrochloride (50.6 mg, 0.364 mmol) and sodium azide (23.68 mg, 0.364 mmol) and the reaction was heated to reflux. After 2 days, the reaction was poured into water (1 ml) and extracted with ethylacetate (10 mL×2). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to an off white solid that was purified by Preparative HPLC method 4 providing (4R,5S)-4-(3-(phenylethynyl)phenyl)-5-(1H-tetrazol-5-yl)oxazolidin-2-one (30 mg, 0.090 mmol, 73.8% yield) 1H NMR (500 MHz, DMSO-d6) δ ppm 5.21-5.55 (m, 2H) 7.10 (br. s., 3H) 7.34 (d, J=7.93 Hz, 1H) 7.39-7.49 (m, 4H) 7.51 (d, J=7.32 Hz, 1H) 7.57 (dd, J=6.41, 3.05 Hz, 2H) 8.27 (s, 1H). Mass spec.: 331.99 (MH)+.

Workup

  1. temperaturethe reaction was heated to reflux
  2. extractionextracted with ethylacetate (10 mL×2)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an off white solid

Sources & evidence

ORD record
ord-ffbf1769a7c248ca833ce03df198a252
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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