Phenylacetyl chloride → HCID 22824716, compound

HRID 1649345Notes

Reaction equation

HRID 1649345 reaction equation
[NH2:1][C@@H:2]([C:4]([NH:6][C:7]1([O:12][CH3:13])[CH2:10][NH:9][C:8]1=[O:11])=[O:5])[CH3:3].C(N(CC)CC)C.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(N(C)C)=O.C1COCC1>[C:21]1([CH2:27][C:28]([N:6]([C:7]2([O:12][CH3:13])[CH2:10][NH:9][C:8]2=[O:11])[C:4](=[O:5])[C@@H:2]([CH3:3])[NH2:1])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 22824710HCID 22824710, compound

Product 1

HCID 22824716HCID 22824716, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

In 2 ml of DMA is dissolved 0.28 g of the 3-(D-alaninamido)-3-methoxy-2-oxoazetidine obtained in Example 16, and 0.30 g of triethylamine is added. To the solution is added a solution of 0.233 g of phenylacetyl chloride in 2 ml of THF under ice-cooling and the mixture is stirred at room temperature for an hour. The mixture is concentrated under reduced pressure and the residue is extracted with ethyl acetate. The extract is purified by silica gel column chromatography to obtain 0.22 g of 3-(N-phenylacetyl-D-alaninamido)-3-methoxy-2-oxoazetidine.

Workup

  1. additionis added
  2. temperaturecooling
  3. concentrationThe mixture is concentrated under reduced pressure
  4. extractionthe residue is extracted with ethyl acetate
  5. customThe extract is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c57aa01bd4fd4e938f2ee9a667bf5e83
Source dataset
uspto-grants-1983_11
Patent number
US04416817

Reaction notes

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