Furfural → HCID 89500527, compound

HRID 925449Notes

Reaction equation

HRID 925449 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]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH:34]=O.[BH4-].[Na+]>CO>[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]([NH:21][CH2:34][C:30]3[O:29][CH:33]=[CH:32][CH:31]=3)[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 7362FurfuralHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 89500570HCID 89500570, compound

Product 1

HCID 89500527HCID 89500527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [5-(5-amino-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (77.5 mg, 0.240 mmol) and NaOAc (59.0 mg, 0.719 mmol) in MeOH (1 ml) was added 2-furaldehyde (0.020 ml, 23.0 mg, 0.240 mmol). The reaction mixture was degassed with Ar and stirred for 15 min at 100° C. in a microwave. After cooling to 0° C., NaBH4 (10.02 mg, 0.252 mmol) was added portionwise and stirring was continued at rt for 1 h. The reaction mixture was quenched with water and diluted with EtOAc. The phases were separated and the aq. layer was twice reextracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered 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. temperatureAfter cooling to 0° C.
  3. stirringstirring
  4. waitwas continued at rt for 1 h
  5. customThe reaction mixture was quenched with water
  6. additiondiluted with EtOAc
  7. customThe phases were separated
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting title compound was purified by FC (cyclohexane:EtOAc 100:0 to 80:20)

Sources & evidence

ORD record
ord-83ef3cc1e16740d8ad3f34db97ab80c9
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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