Phosphoric Acid → HCID 57920482, compound

HRID 1691569Notes

Reaction equation

HRID 1691569 reaction equation
[S:1]1[C:5]([N:6]([CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2.OP(O)(O)=O.[C:35](OC(=O)C)(=[O:37])[CH3:36]>>[C:35]([C:4]1[C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=2[S:1][C:5]=1[N:6]([CH2:20][CH2:21][C:22]([F:25])([F:23])[F:24])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)(=[O:8])=[O:9])(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 1004Phosphoric AcidHCID 7918Acetic Anhydride2×HCID 57920560HCID 57920560, compound

Product 1

HCID 57920482HCID 57920482, compound

Conditions

Temperature
100 °C

Procedure

To compound 385-A (0.388 g, 0.87 mmol) was added acetic anhydride (10 mL) and 85% H3PO4 (0.10 mL), and the reaction was heated at 100° C. for three days. Additional acetic anhydride (10 mL) was added, the reaction mixture heated for an additional 4 more days. The reaction mixture was cooled, concentrated under vacuum, partitioned between EtOAc (100 mL) and saturated NaHCO3 (50 mL), filtered, the organic layer washed with brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (SiO2) eluting with an EtOAc-heptane gradient to afford 0.197 g of compound 385-B as a colorless oil. 1H-NMR (DMSO-d6): δ 2.64 (s, 3H), 2.91-2.72 (m, 2H), 4.01-3.87 (m, 5H), 7.54-7.43 (m, 2H), 7.87 (d, 2H), 7.99-7.92 (m, 1H), 8.19-8.08 (m, 3H); MS: m/z 486.1 (MH+).

Workup

  1. temperaturethe reaction mixture heated for an additional 4 more days
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under vacuum
  4. custompartitioned between EtOAc (100 mL) and saturated NaHCO3 (50 mL)
  5. filtrationfiltered
  6. washthe organic layer washed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by flash column chromatography (SiO2)
  11. washeluting with an EtOAc-heptane gradient

Sources & evidence

ORD record
ord-d099c641def14256a5caa937cfd7f07a
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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