Acetic Acid → HCID 11688567, compound

HRID 1241528Notes

Reaction equation

HRID 1241528 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:18])[CH3:10])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[O:18])[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 11640909HCID 11640909, compound

Product 1

HCID 11688567HCID 11688567, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate (2.24 g) obtained in Step a) was dissolved in THF (20 ml), and thereto was added dropwise acetic acid (2.9 ml) at room temperature, and further thereto was added dropwise a solution of tetra-n-butylammonium fluoride (4.58 g) in THF (18 ml). The mixture was stirred at the same temperature for 3 days, and the reaction solution was diluted with ethyl acetate. The mixture was poured into a cold aqueous sodium hydrogen carbonate solution, and the mixture was extracted and separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give tert-butyl 3-({(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxo-2-azetidinyl}acetyl)benzoate, which was used in the subsequent reaction without further purification.

Workup

  1. extractionthe mixture was extracted
  2. customseparated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-92c93d68ac9d42e28353cdabdc7dc3cb
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

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