HCID 20770837, compound → HCID 20770846, compound

HRID 1296062Notes

Reaction equation

HRID 1296062 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([S:14]C(=O)N(C)C)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1>CO>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([SH:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

3

Reactant 1

HCID 20770837HCID 20770837, compound

Product 1

HCID 20770846HCID 20770846, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 72D (4.04 g, 13.8 mmol) was dissolved in 200 ml methanol. Nitrogen was bubbled for 5 minutes followed by the addition of a 2N NaOH solution (1.4 g/17 ml water). The solution was heated at reflux and tuned brown after 10 minutes. The reaction was concentrated to ca. 50 ml under vacuum and acidified to pH<4 with 2N HCl. The product was extracted into ethyl acetate 2×100 ml, dried over anhydrous sodium sulfate, decanted and concentrated. The crude acid was dissolved into 100 ml anhydrous methanol followed by 5 drops concentrated sulfuric acid. This was heated at reflux for 3 h then cooled to room temp. 500 mg dithiothreitol was added followed by 100 mg sodium borohydride. This was stirred for 1 h and concentrated to an oil. The crude thiol ester was dissolved into 100 ml dichloromethane, filtered through silica and eluted with 300 ml dichloromethane. The filtrate was concentrated and purified by liquid chromatography to give the title product as a yellow oil. MS m/z 222 (M+1).

Workup

  1. customNitrogen was bubbled for 5 minutes
  2. additionfollowed by the addition of a 2N NaOH solution (1.4 g/17 ml water)
  3. temperatureThe solution was heated
  4. temperatureat reflux and tuned brown after 10 minutes
  5. concentrationThe reaction was concentrated to ca. 50 ml under vacuum
  6. extractionThe product was extracted into ethyl acetate 2×100 ml
  7. dry with materialdried over anhydrous sodium sulfate
  8. customdecanted
  9. concentrationconcentrated
  10. dissolutionThe crude acid was dissolved into 100 ml anhydrous methanol
  11. temperatureThis was heated
  12. temperatureat reflux for 3 h
  13. addition500 mg dithiothreitol was added
  14. concentrationconcentrated to an oil
  15. dissolutionThe crude thiol ester was dissolved into 100 ml dichloromethane
  16. filtrationfiltered through silica
  17. washeluted with 300 ml dichloromethane
  18. concentrationThe filtrate was concentrated
  19. custompurified by liquid chromatography

Sources & evidence

ORD record
ord-6b162432ac6145bcba5e7d66d12b0f89
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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