Butylamine → HCID 19920948, compound

HRID 1647698Notes

Reaction equation

HRID 1647698 reaction equation
[CH2:1]([NH:5][C:6](=[O:20])[CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:24][CH2:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27].BrCCC(O)=O.C(N)CCC>O1CCCC1.C(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:20])[CH2:7][CH2:8][N:9]([CH2:24][CH2:25][C:26](=[O:27])[NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 8007ButylamineHCID 115533-Bromopropionic acidHCID 24758Sodium hydrideHCID 4141819HCID 4141819, compoundHCID 19920951HCID 19920951, compound

Product 1

HCID 19920948HCID 19920948, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve N-butyl-3-(toluene-4-sulfonylamino)-propionamide (10 mmol) prepared in Scheme VI, step B in tetrahydrofuran (50 mL) and treat with sodium hydride (10 mmol). Stir the reaction for 30 minutes and add 3-bromo-N-butyl-propionamide (10 mmol) [prepared from amidation between Br(CH2)2CO2H and butyl amine under conditions well known in the art as previously described generally]. Heat the reaction to reflux for 5 hours. After cooling dilute the reaction with methylene chloride (150 mL), rinse with water (100 mL), brine (100 mL), dry over sodium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide N-butyl-3-[(2-butylcarbamoyl-ethyl)-(toluene-4-sulfonyl)-amino]-propionamide.

Workup

  1. customthe reaction for 30 minutes
  2. temperatureHeat
  3. customthe reaction
  4. temperatureto reflux for 5 hours
  5. temperatureAfter cooling
  6. additiondilute
  7. washrinse with water (100 mL), brine (100 mL)
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under vacuum
  11. customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-3bad4e11551c4a648278a41fe60bf939
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

Loading…