Sulfuric Acid → HCID 45085627, compound

HRID 231242Notes

Reaction equation

HRID 231242 reaction equation
[CH2:1]([C@@H:3]1[C@H:6]([C:7]#[C:8][Si](C)(C)C)[NH:5][C:4]1=[O:13])[CH3:2].S(=O)(=O)(O)[OH:15].C(=O)(O)[O-].[Na+]>>[C:7]([C@@H:6]1[NH:5][C:4](=[O:13])[C@@H:3]1[CH2:1][CH3:2])(=[O:15])[CH3:8]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 13891948HCID 13891948, compound

Product 1

HCID 45085627HCID 45085627, compound

Procedure

In a similar manner to that of Example 37, (3R,4R)-3-ethyl-4-trimethylsilylethynyl-2-azetidinone (0.18 g) is reacted with mercuric sulfate (0.05 g) and concentrated sulfuric acid (trace). To the reaction mixture is added sodium bicarbonate (0.1 g) and then evaporated under reduced pressure. The residue is extracted with a mixture of ethyl acetate (30 ml) and THF (30 ml), and then evaporated under reduced pressure. The residue is subjected to a column chromatography on silica gel (eluent: 50% ethyl acetate in hexane) to give (3R,4R)-4-acetyl-3-ethyl-2-azetidinone (0.08 g).

Workup

  1. customevaporated under reduced pressure
  2. extractionThe residue is extracted with a mixture of ethyl acetate (30 ml) and THF (30 ml)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-70ad920ebc0043cd961036cfccf0c50e
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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