Chloroform → HCID 13477587, compound

HRID 370629Notes

Reaction equation

HRID 370629 reaction equation
S(Cl)(Cl)=O.Cl.[CH3:6][O:7][C:8](=[O:15])[CH2:9][CH2:10][C@H:11]([NH2:14])[CH2:12][F:13].C(Cl)(Cl)Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.C(N(CC)CC)C>[C:20]([NH:14][C@H:11]([CH2:12][F:13])[CH2:10][CH2:9][C:8]([O:7][CH3:6])=[O:15])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 24386Thionyl ChlorideHCID 131714255(S)-4-amino-5-fluoropentanoic acid methyl ester, hydrochloride

Product 1

HCID 13477587HCID 13477587, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

1.0 ml of thionyl chloride was added drop-by-drop to a stirred mixture of 650 mg of 4 in 2.5 ml of methanol at room temperature. The resulting mixture was stirred at room temperature for 10 minutes, at reflux for two hours, cooled and stripped of solvent. The residue was mixed with 25 ml of chloroform and the mixture was stirred while 0.47 ml of benzoyl chloride was added drop-by-drop, then 1.2 ml of triethylamine was added, drop-by-drop. The mixture was stirred at room temperature for 16 hours, and the solvent was evaporated. The residue was mixed with 25 ml of water and the mixture was extracted with chloroform. The extract was washed successively with 1N hydrochloric acid, water, 1M sodium bicarbonate solution, and water. It then was dried (MgSO4), the solvent was evaporated, and the residue was recrystallized from methylene chloride/hexane to give 24, as fine white needles, m.p.: 99.5°-100.5° C.

Workup

  1. temperatureat reflux for two hours
  2. temperaturecooled
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature for 16 hours
  5. customthe solvent was evaporated
  6. additionThe residue was mixed with 25 ml of water
  7. extractionthe mixture was extracted with chloroform
  8. washThe extract was washed successively with 1N hydrochloric acid, water, 1M sodium bicarbonate solution, and water
  9. dry with materialIt then was dried (MgSO4)
  10. customthe solvent was evaporated
  11. customthe residue was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-c30ef1814a824d3ebeba1e65f05b6b84
Source dataset
uspto-grants-1985_07
Patent number
US04528028

Reaction notes

Loading…