Hydrochloric Acid → HCID 11654872, compound

HRID 1241526Notes

Reaction equation

HRID 1241526 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:24])[C@@H:14]3[C@H:17]([O:19][Si](C)(C)C)[CH3:18])[C:11]=2[C:25]([O:27][CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:26])[CH:7]=[CH:8][CH:9]=1)=[O:3].Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C1COCC1>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:24])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:25]([O:27][CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:26])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11605795HCID 11605795, compound

Product 1

HCID 11654872HCID 11654872, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

[(2,2-Dimethylpropanoyl)oxy]methyl (5R,6S)-3-[3-(aminocarbonyl)phenyl]-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (11 mg) obtained in Step b) was dissolved in ethyl acetate (2 ml) and THF (2 ml), and thereto was added 0.1N hydrochloric acid under ice-cooling to adjust the pH value thereof to the range of from pH 2 to pH 3. The mixture was vigorously stirred for 20 minutes, and the reaction solution was diluted with ethyl acetate, and poured into a cold aqueous sodium hydrogen carbonate solution. The mixture was extracted and separated, and the organic layer was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel thin layer chromatography (ethyl acetate/acetone=4/1) to give [(2,2-dimethylpropanoyl)oxy]methyl (5R,6S)-3-[3-(aminocarbonyl)phenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (9 mg).

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted
  3. customseparated
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel thin layer chromatography (ethyl acetate/acetone=4/1)

Sources & evidence

ORD record
ord-42d3f08e582d4d8285f1df17197aebca
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

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