Sodium Bicarbonate → HCID 54300876, compound

HRID 610468Notes

Reaction equation

HRID 610468 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:7][N:6]([O:8][C:9](=[O:11])[CH3:10])[C:5]1=[O:12].[N+](=C(C(=O)CC)C(OCC1C=CC=CC=1)=[O:17])=[N-].C([O-])(O)=O.[Na+]>ClCCl.[Cl-].[Zn+2].[Cl-]>[OH:17][C:4]1([CH2:3][CH3:2])[CH2:7][N:6]([O:8][C:9](=[O:11])[CH3:10])[C:5]1=[O:12]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 54381089HCID 54381089, compoundHCID 57318449HCID 57318449, compound

Product 1

HCID 54300876HCID 54300876, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the hydroxyethyl acetoxy azetidinone of Formula 10 (112 mg, 0.65 mmol) and silyl enol ether of benzyl 2-diazo-3-oxopentanoate (394 mg, 1.3 mmol) was dissolved in sieve dried dichloromethane (2 mL) and added to a suspension of fused (under vacuum) zinc chloride (55 mg, 0.4 mmol) in dichloromethane (2 mL). After refluxing gently for 12 hours, the mixture was poured into saturated NaHCO3 (50 mL) and extracted with ethyl acetate (100 mL). The ethyl acetate layer was washed with brine, dried over MgSO4, and concentrated to an oil. Chromatography on silica gel gave the compound of Formula 12 in 77% yield.

Workup

  1. additionadded to a suspension
  2. temperatureAfter refluxing gently for 12 hours
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-37a4cafd512d42de8379d5fc73f9be42
Source dataset
uspto-grants-1999_12
Patent number
US05998612

Reaction notes

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