Phosphorus oxychloride → HCID 69085465, compound

HRID 2362380Notes

Reaction equation

HRID 2362380 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]([NH2:23])=O)[O:3]1.P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>ClCCl>[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:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:8]=2)[C@@H:4]([C:21]#[N:23])[O:3]1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69083790HCID 69083790, compound

Product 1

HCID 69085465HCID 69085465, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carboxamide (80 mg, 0.261 mmol) in dichloromethane (2 mL) was added phosphorus oxychloride (0.243 mL, 2.61 mmol). The reaction was heated to reflux for 4 h and sodium bicarbonate (sat) was added until pH 7. The reaction mixture was back extracted with dichloromethane (3×5 mL) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to yield a yellow wax that was purified by Preparative HPLC Method 6 providing (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carbonitrile (53 mg, 0.178 mmol, 68.3% yield) 1H NMR (500 MHz, DMSO-d6) δ ppm 5.36 (d, J=4.27 Hz, 1H) 5.63 (d, J=4.27 Hz, 1H) 7.39-7.49 (m, 4H) 7.52 (t, J=7.93 Hz, 1H) 7.56-7.64 (m, 4H) 8.76 (br. s., 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 h
  3. extractionThe reaction mixture was back extracted with dichloromethane (3×5 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow wax that

Sources & evidence

ORD record
ord-e479399bc4e44576ad6668c4aad7f9b0
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

Loading…