Phosphorus oxychloride → HCID 59598981, compound

HRID 2102275Notes

Reaction equation

HRID 2102275 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=O)[NH:10][C:9]([NH2:14])=[N:8][C:7]=2[N:6]([C@@H:15]2[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]2[O:17][C:18](=[O:20])[CH3:19])[C:5]1=[O:33])[CH:2]=[CH2:3].P(Cl)(Cl)([Cl:36])=O>>[CH2:1]([N:4]1[C:12]2[C:7](=[N:8][C:9]([NH2:14])=[N:10][C:11]=2[Cl:36])[N:6]([C@@H:15]2[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]2[O:17][C:18](=[O:20])[CH3:19])[C:5]1=[O:33])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136108950HCID 136108950, compound

Product 1

HCID 59598981HCID 59598981, compoundYield 41%

Conditions

Temperature
75 °C

Procedure

Compound 40 (0.65 g, 1.39 mmol) was dissolved in phosphorus oxychloride (10 mL) and heated to 75° C. for 16 h. The reaction mixture was concentrated under vacuum and the crude product dissolved in DCM. The mixture was then washed with NaHCO3 solution, brine, dried (MgSO4) and filtered. The filtrate was concentrated under vacuum and purified by flash chromatography using 10 to 50% gradient of ethyl acetate in hexanes. Removal of the solvent afforded 280 mg (41%) of the desired product 41: 1H NMR (400 MHz, CDCl3) δ 6.04 (d, J=4.0 Hz, 1H), 6.03 (t, J=5.6 Hz, 1H), 5.87 (m, 1H), 5.86 (t, J=5.6 Hz, 1H), 5.18 (m, 4H), 4.59 (d, J=8.0 Hz, 2H), 4.45 (d, J=7.6 Hz, 1H), 4.31 (m, 2H), 2.10 (s, 3H), 2.08 (s, 3H), 2.04 (s, 3H); MS (+)-ES [M+H]+ 484.2 m/z.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe crude product dissolved in DCM
  3. washThe mixture was then washed with NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. custompurified by flash chromatography
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-97e30599711a4e108457f539cd754bf7
Source dataset
uspto-grants-2009_08
Patent number
US07576068B2

Reaction notes

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