Water → HCID 22875336, compound

HRID 2256090Notes

Reaction equation

HRID 2256090 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].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

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 22875337HCID 22875337, compound

Product 1

HCID 22875336HCID 22875336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 191 mg of cis-8-tert-butoxycarbonyl-5-[(1R)-1-phenylethylamino]-4-oxo-2-oxa-5,8-diazabicyclo[4.3.0]nonane 13a in 6 ml of tetrahydrofuran was added 1 ml of 1M diborane tetrahydrofuran complex dropwise. The mixture was stirred at 5° C. for 3 days. To an ice-cooled reaction mixture was added 15 ml of water and 10 ml of saturated potassium carbonate aqueous solution, and the mixture was stirred. The mixture was extracted by chloroform and the organic layer was separated. The organic layer was washed by saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and 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 14a weighing 103 mg was obtained.

Workup

  1. customreaction mixture
  2. stirringthe mixture was stirred
  3. extractionThe mixture was extracted by chloroform
  4. customthe organic layer was separated
  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-4aba39f16cc345c49db16f9dc96a905e
Source dataset
uspto-grants-1997_08
Patent number
US05654318

Reaction notes

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