2-Methyl-2-butene → HCID 67439630, compound

HRID 1664856Notes

Reaction equation

HRID 1664856 reaction equation
P([O-])(O)(O)=O.[Na+].Cl([O-])=[O:8].[Na+].[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C@H:19]1[CH2:25][N:24]2[C:26]([CH:29]=[O:30])=[CH:27][N:28]=[C:23]2[C@H:22]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:20]1.CC(=CC)C>O1CCCC1.O.C(O)(C)(C)C>[C:34]([O:33][C:32]([NH:31][C@@H:22]1[CH2:21][CH2:20][C@@H:19]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=2[F:11])[CH2:25][N:24]2[C:26]([C:29]([OH:8])=[O:30])=[CH:27][N:28]=[C:23]12)=[O:38])([CH3:35])([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 59722730HCID 59722730, compound

Product 1

HCID 67439630HCID 67439630, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium dihydrogen phosphate (127 mg, 0.92 mmol) and sodium chlorite (42 mg, 0.46 mmol) were added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-formyl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (45 mg, 0.12 mmol) in tetrahydrofuran (0.8 mL), water (0.8 mL), tert-butanol (0.2 mL), and 2-methyl-2-butene (0.2 mL). After 3 h of vigorously stirring, the reaction mixture was quenched with saturated solution of ammonium chloride. The mixture was extracted with ethyl acetate (3×), and the combined organic extracts were washed with water, saturated brine, dried over sodium sulfate, filtered and concentrated. MS 408.1 (M+1).

Workup

  1. customthe reaction mixture was quenched with saturated solution of ammonium chloride
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic extracts were washed with water, saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b9afe29bad64f33a849d43481957aaf
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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