Acetic Acid → HCID 54000860, compound

HRID 648187Notes

Reaction equation

HRID 648187 reaction equation
[NH2:1][CH2:2][CH:3]([OH:16])[CH2:4][O:5][C:6]1[S:7][C:8]([C:11](=O)[N:12]([CH3:14])[CH3:13])=[CH:9][N:10]=1.C(O)(=O)C.[H][H].O>O1CCCC1.C(Cl)(Cl)Cl.CO>[NH2:1][CH2:2][CH:3]([OH:16])[CH2:4][O:5][C:6]1[S:7][C:8]([CH2:11][N:12]([CH3:13])[CH3:14])=[CH:9][N:10]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 20482388HCID 20482388, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54000860HCID 54000860, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 11 (2.0 g, 8.2 mmol) can be added to a solution of borane dimethylsulfide complex (2.5 g, 33 mmol) in 25 ml of dry tetrahydrofuran at room temperature. After one hour, the mixture can be heated to reflux for 4 hours under nitrogen. The resulting suspension can then be cooled to 0° C., cautiously treated dropwise with 5 ml of glacial acetic acid and, after hydrogen evolution ceases, the solution can be heated to reflux for 8 hours. The mixture can then be cooled to 0° C., cautiously treated with water and concentrated in vacuo. The aqueous residue can be extracted with ether, basified with 10 N sodium hydroxide and reextracted with methylene chloride-ethanol. The methylene chloride extracts can then be combined, dried (Na2SO4), filtered and concentrated in vacuo to give the crude product. The pure title compound can be obtained by chromatography on silica gel with 20% methanol in chloroform.

Workup

  1. temperaturethe mixture can be heated
  2. temperatureto reflux for 4 hours under nitrogen
  3. temperatureto reflux for 8 hours
  4. temperatureThe mixture can then be cooled to 0° C.
  5. concentrationconcentrated in vacuo
  6. extractionThe aqueous residue can be extracted with ether
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product

Sources & evidence

ORD record
ord-e42e232710ca4df19beb9bdf7f992b17
Source dataset
uspto-grants-1983_10
Patent number
US04411899

Reaction notes

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