HCID 19980849, compound → HCID 19980861, compound

HRID 1461478Notes

Reaction equation

HRID 1461478 reaction equation
[O:1]=[S:2]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH:13]=[O:14])[CH2:5][CH:4]([OH:15])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[O:16]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH:13]=[O:14])[CH2:5][C:4](=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 19980849HCID 19980849, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 19980861HCID 19980861, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1,1-dioxo-5-N-formyl-3-hydroxy -2,3,4,5-tetrahydro-[1,5]-benzothiazepine (0.443 g, 1.83 mmole) from Example 15, in 5 mL of acetone was treated with Jones reagent (0.54 mL, 1.40 mmole), and the solution was heated to reflux for 15 minutes. An additional 0.15 mL of Jones reagent was added and the reaction was heated for 20 minutes longer. The cooled solution was filtered through MgSO4, and the solvents were removed under reduced pressure. The residue was triturated with chloroform and filtered. Evaporation of the filtrate afforded the product (0.418 g, 95% yield) D.C.I.M.S. 240 [M+H].

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 15 minutes
  3. temperaturethe reaction was heated for 20 minutes longer
  4. filtrationThe cooled solution was filtered through MgSO4
  5. customthe solvents were removed under reduced pressure
  6. customThe residue was triturated with chloroform
  7. filtrationfiltered
  8. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-a1ee77f96521437682365a9b68b67d75
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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