Hydrogen Peroxide → HCID 117982177, compound

HRID 1776114Notes

Reaction equation

HRID 1776114 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH2:18][Se]C2C=CC=CC=2[N+]([O-])=O)[C@@H:12]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:11]([CH3:36])[O:10][C:9]1=[O:37])([CH3:4])([CH3:3])[CH3:2].OO>C1COCC1>[C:1]([O:5][C:6](=[O:38])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH:17]=[CH2:18])[C@@H:12]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@H:11]([CH3:36])[O:10][C:9]1=[O:37])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 131734757HCID 131734757, compound

Product 1

HCID 117982177HCID 117982177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl((3S,7R,8R,9S)-9-methyl-7-(2-((2-nitrophenyl)-selanyl)ethyl)-2-oxo-8-phenoxyoxonan-3-yl)carbamate (284 mg, 0.480 mmol) in THF (4.8 mL) was added 30% aqueous hydrogen peroxide (H2O2 392 μl, 3.84 mmol), and the resulting bright yellow solution was stirred at room temperature for 3 d. The reaction was cooled to 0° C. (icewater bath), quenched with sat. aqueous NaHSO3 solution (4 mL), diluted with H2O (20 mL), and extracted with EtOAc (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, and concentrated to the title compound as an orange solid (134.9 mg, 72%): 1H NMR (400 MHz, CDCl3) δ 7.34-7.19 (m, 2H), 7.02-6.86 (m, 3H), 5.76 (ddd, J=17.2, 10.3, 8.0 Hz, 1H), 5.17-5.06 (m, 2H), 5.03 (d, J=17.1 Hz, 1H), 4.94 (d, J=10.4 Hz, 1H), 4.28 (t, J=8.8 Hz, 1H), 4.25-4.17 (m, 1H), 2.56-2.41 (m, 1H), 2.27 (dt, J=13.5, 6.6 Hz, 1H), 1.85 (td, J=14.6, 7.1 Hz, 1H), 1.75 (dt, J=14.8, 7.3 Hz, 1H), 1.65 (s, 1H), 1.44 (s, 9H), 1.33 (d, J=6.4 Hz, 3H), 1.31-1.17 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 173.35, 159.33, 138.51, 129.49, 121.10, 116.18, 115.78, 99.98, 80.46, 74.39, 53.05, 47.47, 34.13, 31.07, 28.34, 19.66, 18.36; HRMS-ESI (m/z) ([M+Na]+) calcd for C22H31NO5Na, 412.2094, found 412.2106.

Workup

  1. temperatureThe reaction was cooled to 0° C. (icewater bath)
  2. customquenched with sat. aqueous NaHSO3 solution (4 mL)
  3. additiondiluted with H2O (20 mL)
  4. extractionextracted with EtOAc (3×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to the title compound as an orange solid (134.9 mg, 72%)

Sources & evidence

ORD record
ord-9aff345708d940f18f1cd67871a9d977
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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