Hydrogen Peroxide → HCID 89955814, compound

HRID 1481282Notes

Reaction equation

HRID 1481282 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:23]=[C:22]2[C:9]([C:10]3[CH:34]=[C:14]([C@@H:15]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:16][CH:17]=[CH:18][C@@H:19]([CH3:25])[C:20](=[O:24])[NH:21]2)[N:13]=[CH:12][CH:11]=3)=[CH:8][CH:7]=1)=[O:4].C([O-])(=[O:37])C.[Na+].OO>C1COCC1.O>[OH:37][CH:17]1[CH2:16][C@H:15]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:14]2=[CH:34][C:10](=[CH:11][CH:12]=[N:13]2)[C:9]2[C:22](=[CH:23][C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])=[CH:7][CH:8]=2)[NH:21][C:20](=[O:24])[C@H:19]([CH3:25])[CH2:18]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 517045Sodium AcetateHCID 89955554HCID 89955554, compound

Product 1

HCID 89955814HCID 89955814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-[(10R,11E,14S)-5-[(methoxycarbonyl)amino]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(18),2,4,6,11,15(19),16-heptaen-14-yl]carbamate (634 mg, 1.36 mmol) 1H in THF (13.6 mL) at 0° C. was added borane tetrahydrofuran complex (4.08 mL, 4.08 mmol) dropwise. The reaction was allowed to warm up to rt and stirred for 2.5 h. The reaction mixture was cooled to 0° C. and added sodium acetate (9.06 ml, 27.2 mmol), followed by hydrogen peroxide (4.16 mL, 40.8 mmol) dropwise. The reaction was warmed up to rt and stirred at for 8 h. The mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-10% MeOH/DCM) to yield a mixture of two products 22A and 22B (323 mg, 49%) as a light grey solid. MS (ESI) m/z: 485.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe reaction was warmed up to rt
  3. stirringstirred at for 8 h
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (0-10% MeOH/DCM)
  10. customto yield

Sources & evidence

ORD record
ord-ba007cc7eb93441fa521a0b85d172318
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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