Thiirane → HCID 19920939, compound

HRID 1647700Notes

Reaction equation

HRID 1647700 reaction equation
[CH2:1]([NH:5][C:6](=[O:19])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:12](=[O:18])[NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH3:4].[CH2:20]1[S:22][CH2:21]1>O1CCCC1>[CH2:1]([NH:5][C:6](=[O:19])[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][C:12](=[O:18])[NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:20][CH2:21][SH:22])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 9865ThiiraneHCID 19920949HCID 19920949, compound

Product 1

HCID 19920939HCID 19920939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve N-butyl-3-(2-butylcarbamoyl-ethylamino)-propionamide (10 mmol) prepared in Scheme VI, step D in tetrahydrofuran (50 mL) and add dropwise ethylene sulfide (22 mmol). Heat the reaction to reflux for 4 hours. After cooling, concentrate the reaction under vacuum and purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide N-butyl-3-[(2-butylcarbamoyl-ethyl)-(2-mercapto-ethyl)amino]-propionamide.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 4 hours
  4. temperatureAfter cooling
  5. concentrationconcentrate
  6. customthe reaction under vacuum
  7. custompurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-985ee0d654c64ef6a3a5aab2aeb8b345
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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