Thionyl Chloride → HCID 58137029, compound

HRID 2194375Notes

Reaction equation

HRID 2194375 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>ClCCl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([Cl:22])=[O:17])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66673547HCID 66673547, compound

Product 1

HCID 58137029HCID 58137029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.97 g (7.43 mmol) of 5-[[(benzyloxy)carbonyl](methyl)amino]valeric acid are dissolved in 30 ml of dichloromethane, and 4.9 ml (67.3 mmol) of thionyl chloride are added. The mixture is heated under reflux for 1 h. It is then concentrated in vacuo, and the residue is again mixed with dichloromethane and concentrated once again. A viscous oil remains and is dried under high vacuum. 2 g (95% of theory) of the target compound are obtained and are reacted further without further purification and characterization.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt is then concentrated in vacuo
  4. additionthe residue is again mixed with dichloromethane
  5. concentrationconcentrated once again
  6. customA viscous oil remains and is dried under high vacuum
  7. custom2 g (95% of theory) of the target compound are obtained
  8. customare reacted further without further purification and characterization

Sources & evidence

ORD record
ord-0758cd452ac14fc8b69bec17e861391d
Source dataset
uspto-grants-2012_12
Patent number
US08334284B2

Reaction notes

Loading…