Aluminum → HCID 13019671, compound

HRID 2287172Notes

Reaction equation

HRID 2287172 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 mixed 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 hydrogencarbonate 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 hydrogencarbonate 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-cd5425f5d8b6499dba5e7cd337250871
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

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