Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 24944536, compound

HRID 2077041Notes

Reaction equation

HRID 2077041 reaction equation
[F:1][C:2]([F:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:3]1[NH:4][C:5](=[O:21])[C:6]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8][C:7]=2[N:20]=1.F[B-](F)(F)F.[CH3:34][O+](C)C>>[F:1][C:2]([F:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:3]1[N:4]=[C:5]([O:21][CH3:34])[C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[N:20]=1

Participants

3

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 136058097HCID 136058097, compound

Product 1

HCID 24944536HCID 24944536, compound

Procedure

To a solution of tert-butyl 2-[difluoro(phenyl)methyl]-4-oxo-3,4,5,6,8,9-hexahydro-7H-pyrimido[4,5-d]azepine-7-carboxylate of Preparation 8, Step A (535 mg, 1.37 mmol) was added trimethyloxonium tetrafluoroborate (3 eq, 606 mgs 4.10 mmol) and the reaction mixture was stirred overnight at room temperature, after which time an orange solid had precipitated. The reaction mixture was quenched with saturated NaHCO3 (aq) and stirred rapidly until a complete solution was attained. The organic layer was collected, dried over MgSO4, filtered and dried in vacuo to give a brown oil. This material was chromatographed on silica, eluting with ethyl acetate/10% methanol, then dichloromethane/methanol/ammonia, 95/5/0.5. The relevant fractions were combined and evaporated in vacuo to give a coloured oil (quantitative yield).

Workup

  1. customafter which time an orange solid had precipitated
  2. customThe reaction mixture was quenched with saturated NaHCO3 (aq)
  3. stirringstirred rapidly until a complete solution
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customdried in vacuo
  8. customto give a brown oil
  9. customThis material was chromatographed on silica
  10. washeluting with ethyl acetate/10% methanol
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-69c62b88fc7340289267cca98f2cf91b
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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