Hydrogen Peroxide → HCID 21060007, compound

HRID 1241474Notes

Reaction equation

HRID 1241474 reaction equation
OO.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[N:16]([C@@H:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH3:18])[C:15](=[O:26])[CH:14]([Se]C3C=CC=CC=3)[CH:13]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:12][C:11]2=[O:40])=[CH:6][CH:5]=1>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[N:16]([C@@H:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH3:18])[C:15](=[O:26])[CH:14]=[C:13]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:12][C:11]2=[O:40])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86600979HCID 86600979, compound

Product 1

HCID 21060007HCID 21060007, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrogen peroxide (500 μL, 30% in water) was slowly added to a solution of (3S)-1,3,6,7-tetrahydro-3-(4-chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-phenyl-6-(phenylseleno)-1,4-diazepine-2,5-dione (300 mg, 0.49 mmol) in tetrahydrofuran (6 mL). After 20 min., the solvent was evaporated under reduced pressure and the residue was partitioned between 1N sodium hydrogenocarbonate (20 mL) and ethyl acetate (50 mL), dried (Na2SO4) and evaporated. Purification by column chromatography (AcOEt/hexanes/CH2Cl2, 1:2:2) afforded the title compound (200 mg, 85%) as a colorless powder: 1H NMR (400 MHz, CDCl3) δ 1.70 (d, J=7.2 Hz, 3H, CH3), 5.28 (s, 1H, CH), 5.70 (d, J=1.6 Hz, 1H, CH), 6.35 (q, J=7.2 Hz, 1H, CH), 6.83 (d, J=8.8 Hz, 2H, ArH), 7.09 (d, J=8.8 Hz, 2H, ArH), 7.18–7.42 (m, 7H, ArH), 7.53 (d, J=8.8 Hz, 2H, ArH). Mass spectrum (LCMS, ESI pos.): Calcd for C25H20Cl2N2O2: 450.0; found: 451.0 (M+H)+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between 1N sodium hydrogenocarbonate (20 mL) and ethyl acetate (50 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification by column chromatography (AcOEt/hexanes/CH2Cl2, 1:2:2)

Sources & evidence

ORD record
ord-33d585ea21ea436c8232e936d75eb4bd
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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