Ethyl Acetate → HCID 19605321, compound

HRID 1603665Notes

Reaction equation

HRID 1603665 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:13][CH:14]2[NH:17][C:16](=[O:18])[CH2:15]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[CH3:19][O:20][C:21](=[O:24])[CH2:22]Br.C(OCC)(=O)C>CN(C=O)C>[CH3:19][O:20][C:21](=[O:24])[CH2:22][N:17]1[CH:14]([S:13][C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)[CH2:15][C:16]1=[O:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 19605239HCID 19605239, compound

Product 1

HCID 19605321HCID 19605321, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.5 g, 12 mmol) in dry DMF (10 ml) was cooled to -5° C. and a solution of 4-(3,4-dimethoxyphenylthio)azetidin-2-one (3 g, 12 mmol) in dry DMF (20 ml) was added dropwise over 15 mins under a nitrogen atmosphere at -5° C. After 15 mins methylbromoacetate (2 g, 12 mmol) was added in one portion, and the mixture stirred for 30 mins at room temperature. The reaction mixture was carefully poured into brine/ice water and ethyl acetate (100 ml) was added. The organic layer was washed with brine (x2), dried (MgSO4) and evaporated to a yellow oil which was purified by flash column chromatography eluted with petroleum ether/ethyl acetate to give the product as a yellow oil (0.96 g, 25% yield).

Workup

  1. additionwas added
  2. washThe organic layer was washed with brine (x2)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a yellow oil which
  5. customwas purified by flash column chromatography
  6. washeluted with petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-045b2e149d9340d9b9a7ce0c9237f243
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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