Aluminum → HCID 13019671, compound

HRID 971399Notes

Reaction equation

HRID 971399 reaction equation
[C:1]([C:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[N:6]=1)([O:3][CH3:4])=[O:2].[Al]>O1CCCC1>[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:24])[CH3:25])[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[NH:6]1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 13019670HCID 13019670, compound

Product 1

HCID 13019671HCID 13019671, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 75 g of benzyl α-(3-carbomethoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-α-isopropylideneacetate in 900 ml of tetrahydrofuran containing 5% water is mix with aluminium amalgam which has been prepared from 26.3 g of aluminium and 2.5% aqueous solution of mercuric chloride, and the mixture stirred under ice-cooling for 20 minutes. The reaction mixture is filtrated through Hyflo Super Cel, diluted with ethyl acetate, washed with an aqueous solution of sodium hydrogen-carbonate and water, dried on sodium sulfate, concentrated and then mixed with ether. The resulting crystals are collected by filtration to yield 47.02 g of benzyl α-(3ξ-carbomethoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 62.4% yield.

Workup

  1. temperaturecooling for 20 minutes
  2. filtrationThe reaction mixture is filtrated through Hyflo Super Cel
  3. additiondiluted with ethyl acetate
  4. washwashed with an aqueous solution of sodium hydrogen-carbonate and water
  5. customdried on sodium sulfate
  6. concentrationconcentrated
  7. additionmixed with ether
  8. filtrationThe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-2d737439fc3d45babd03d66c42dd22ab
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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