Water → HCID 22875336, compound

HRID 2256092Notes

Reaction equation

HRID 2256092 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([N:11]([NH:18][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[C:12](=O)[CH2:13][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B#B.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([N:11]([NH:18][C@@H:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH3:20])[CH2:12][CH2:13][O:14]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6328200DiboronHCID 22875337HCID 22875337, compound

Product 1

HCID 22875336HCID 22875336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.32 g of cis-8-tert-butoxycarbonyl -5-[(1R)-1-phenylethylamino]-4-oxo-2-oxa-5,8-diazabicyclo[4.3.0]nonane 13b in 6 ml of tetrahydrofuran was added 19.2 ml of 1M diborane tetrahydrofuran complex dropwise under ice-cooling. The mixture was stirred at room temperature overnight. To the mixture was added 5 ml of the diborane solution mentioned above and the mixture was stirred at room temperature for 2 hours. To an ice-cooled reaction mixture was added water and saturated potassium carbonate aqueous solution. The mixture was extracted by ethyl acetate. The organic layer was washed by saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. A residue was subjected to silica gel column chromatography. From an eluant of a mixture of hexane and ethyl acetate (3:1 by volume), the titled compound 14b weighing 2.17 g was obtained.

Workup

  1. temperaturecooling
  2. stirringwas stirred at room temperature for 2 hours
  3. customreaction mixture
  4. extractionThe mixture was extracted by ethyl acetate
  5. washThe organic layer was washed by saturated sodium chloride aqueous solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. additionFrom an eluant of a mixture of hexane and ethyl acetate (3:1 by volume)
  9. customwas obtained

Sources & evidence

ORD record
ord-722ca4a60e2149309cbc0f60f04eea26
Source dataset
uspto-grants-1997_08
Patent number
US05654318

Reaction notes

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