Acetic Acid → HCID 86596173, compound

HRID 1271106Notes

Reaction equation

HRID 1271106 reaction equation
[O:1]=[C:2]1[N:8]2[C@H:4]([CH2:5][C:6]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][Si](C)(C)C)[CH:23]=3)=[C:7]2[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C@H:3]1[C@H:33]([O:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH3:34].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[OH:28][C:24]1[CH:23]=[C:22]([C:6]2[CH2:5][C@H:4]3[N:8]([C:2](=[O:1])[C@@H:3]3[C@H:33]([O:35][Si:36]([CH3:38])([CH3:39])[CH3:37])[CH3:34])[C:7]=2[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 86596174HCID 86596174, compound

Product 1

HCID 86596173HCID 86596173, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitrobenzyl (5R,6S)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-3-{3-[(trimethylsilyl)oxy]phenyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (500 mg) in THF (8.6 ml) was added at −78° C. acetic acid (51 mg). Thereto was dropped 1M tetrabutylammonium fluoride/THF solution (0.86 ml), and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was poured into a mixture of a cold aqueous sodium hydrogencarbonate (72 mg) and ethyl acetate. The mixture was extracted and separated by a separating funnel. The organic layer was washed with a cold saturated aqueous sodium chloride solution (three times) and cold water in the order, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-nitrobenzyl (5R,6S)-3-(3-hydroxyphenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate. This product was used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted
  2. customseparated by a separating funnel
  3. washThe organic layer was washed with a cold saturated aqueous sodium chloride solution (three times) and cold water in the order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b947f7c5af4046dabdfd362ede8a2995
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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