Hydrogen Peroxide → HCID 25056011, compound

HRID 2101756Notes

Reaction equation

HRID 2101756 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@@H:28]([C:45]3[CH:49]=[CH:48][O:47][N:46]=3)[CH2:29][C:30](N3[C@@H](CC4C=CC=CC=4)COC3=O)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C1C[O:53]CC1.O.OO.[OH-].[Li+].[O-]S([O-])=O.[Na+].[Na+]>>[CH3:3][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@@H:28]([C:45]3[CH:49]=[CH:48][O:47][N:46]=3)[CH2:29][C:30]([OH:53])=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:4]

Participants

7

Reactant 6

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 57672388HCID 57672388, compound

Product 1

HCID 25056011HCID 25056011, compoundYield 48%

Procedure

To a stirred solution of 6.6 (0.0282 g, 0.043 mmol) in THF (3.00 mL, 37 mmol) and water (1.00 mL, 56 mmol) at 0° C. was added 35% hydrogen peroxide (0.025 mL, 0.26 mmol) followed by lithium hydroxide (0.0020 g, 0.085 mmol). Stirring continued for 1 hour and 40 minutes. A saturated solution of Na2SO3 was added, and stirring was continued at 0° C. for 30 minutes. The mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-30% EtOAc/hexane) to give compound 6 as a clear oil (0.0103 g, 48% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.28 (1H, d, J=1.6 Hz), 7.58 (1H, d, J=8.6 Hz), 7.40 (1H, dd, J=8.2, 2.0 Hz), 7.17 (2H, d, J=8.8 Hz), 6.86 (1H, dt, J=8.0, 3.9 Hz), 6.78 (1H, dd, J=5.9, 3.1 Hz), 6.07 (1H, d, J=1.6 Hz), 4.99 (2H, s), 4.54 (1H, dd, J=7.9, 7.4 Hz), 3.79 (3H, s), 3.35 (1H, dd, J=16.6, 7.9 Hz), 2.98 (1H, dd, J=16.4, 7.4 Hz), 1.23 (9H, s). MS ESI (neg.) m/e: 502.1 (M−H)+.

Workup

  1. stirringstirring
  2. waitwas continued at 0° C. for 30 minutes
  3. extractionThe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-e3a2b133bb4542cab2d176f0cb2fba43
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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