Hydrochloric Acid → HCID 58691142, compound

HRID 2376657Notes

Reaction equation

HRID 2376657 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:23])[C@@H:13]3[C@H:16]([O:18][Si](C)(C)C)[CH3:17])[C:10]=2[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH:6]=[CH:7][CH:8]=1.Cl.C(=O)([O-])O.[Na+]>C1COCC1.O.[Cl-].[Na+].O>[OH:18][C@@H:16]([C@H:13]1[C:12](=[O:23])[N:11]2[C@@H:14]1[CH2:15][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:10]2[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58691148HCID 58691148, compound

Product 1

HCID 58691142HCID 58691142, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Allyl (5R,6S)-3-(3-methoxyphenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.70 g, 4.09 mmol) prepared by step c) was dissolved in THF (40 ml) and water (20 ml), and the mixture was cooled in a water bath and thereto was gradually dropped 1N hydrochloric acid using a pH meter so as to become pH=2.5. After 15 minutes, thereto were added an aqueous saturated sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml), and the mixture was extracted with chloroform (50 ml×3 times). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated to give allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(3-methoxyphenyl)-7-oxo1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.37 g, 3.99 mmol, yield 98%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with chloroform (50 ml×3 times)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d5d7f85b8da426db4881ad1908314b3
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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