Phosphorus oxychloride → HCID 53677500, compound

HRID 1742743Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8](=[O:21])[CH:9]=[CH:10][CH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2.[C:22](=O)(O)[O-:23].[Na+]>CN(C=O)C.O>[CH3:6][O:7][C:8](=[O:21])[CH:9]=[CH:10][CH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([CH:22]=[O:23])=[CH:15][NH:16]2

Participants

Conditions

Temperature: 35 °C

Procedure

Phosphorous oxychoride (0.65 g, 4.16 mmol) was added dropwise to DMF (3 mL) at 0° C. After 0.5 hour, Example 7b (0.81 g, 3.70 mmol) in DMF (3 mL) was added at 0° C., then the mixture warmed to 35° C. for 0.75 hour. The solution was cooled to ambient temperature and crushed ice (10 g) was added. Solid sodium bicarbonate was added and to pH 8, the mixture diluted with water (100 mL), and the aqueous extracted with ethyl acetate (3×). The organic phase was separated, dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The residue was chromatographed (eluting ethyl acetate/hexanes) to yield 0.39 g of the title compound as a purple solid; MS(CI/NH3) m/e 244 (M+H)+. 1H NMR(CDCl3, 300 MHz) δ3.68 (s, 3H), 4.26 (m, 2H), 5.14 (m, 1H), 7.06 (d, 1H), 7.18 (m, 3H), 7.84 (d, 1H), 9.09 (br s, 1H), 9.88 (s, 1H).

Workup

customwas added at 0° C.
temperatureThe solution was cooled to ambient temperature
additionwas added
extractionthe aqueous extracted with ethyl acetate (3×)
customThe organic phase was separated
dry with materialdried over anhydrous sodium sulfate
customthe solvent removed in vacuo
customThe residue was chromatographed
wash(eluting ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f1e7c7cfdffb41ae9142f9f299d1fab3
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340802

Reaction notes

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