Water → HCID 89500641, compound

HRID 925447Notes

Reaction equation

HRID 925447 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N-:38]=[N+:39]=[N-:40].[Na+]>CCO.[Cu]I>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([N:38]=[N+:39]=[N-:40])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 23667548Sodium AscorbateHCID 89500427HCID 89500427, compound

Product 1

HCID 89500641HCID 89500641, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (5.0 g, 12.91 mmol) in EtOH (50 ml) was homogenized in an ultrasound bath for 10 min. To this suspension was added water (22 ml), cyclohexane dimethyldiamine (0.611 ml, 0.551 g, 3.87 mmol), sodium ascorbate (0.512 g, 2.58 mmol), sodium azide (3.36 g, 51.6 mmol) and CuI (0.492 g, 2.58 mmol). The reaction mixture was degassed with Ar and heated for 1 h at 70° C., then cooled to rt, filtered through silica gel and concentrated. The resulting title compound was purified by FC (cyclohexane:EtOAc 100.0 to 80:20).

Workup

  1. customThe reaction mixture was degassed with Ar
  2. temperaturecooled to rt
  3. filtrationfiltered through silica gel
  4. concentrationconcentrated
  5. customThe resulting title compound was purified by FC (cyclohexane:EtOAc 100.0 to 80:20)

Sources & evidence

ORD record
ord-fdaf8a3f6f7b4403804d97544e552786
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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