Aluminum → Methyl alpha-(3xi-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetate

HRID 971400Notes

Reaction equation

HRID 971400 reaction equation
[C:1]([C:11]1[O:17][CH:16]2[CH:13]([C:14](=[O:26])[N:15]2[C:18](=[C:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[N:12]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Al]>O1CCCC1>[C:1]([CH:11]1[O:17][CH:16]2[CH:13]([C:14](=[O:26])[N:15]2[C:18](=[C:23]([CH3:24])[CH3:25])[C:19]([O:21][CH3:22])=[O:20])[NH:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 23459417Methyl alpha-(3-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-alpha-isopropylideneacetate

Product 1

HCID 70561235Methyl alpha-(3xi-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-alpha-isopropylideneacetateYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.00 g of methyl α-(3-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)-α-isopropylideneacetate in 100 ml of tetrahydrofuran containing 5% water is added aluminium amalgam prepared from 4 g of aluminium and 0.5 g of mercuric chloride, and the mixture stirred at room temperature for 1.5 hours. The reaction mixture is dried on magnesium sulfate and concentrated under reduced pressure to yield 4.92 g of methyl α-(3ξ-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate as crude product in 98.4% yield.

Workup

  1. customThe reaction mixture is dried on magnesium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ee7efdca5d24afba7e92b5310f04068
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

Loading…