Thionyl Chloride → HCID 58137029, compound

HRID 421573Notes

Reaction equation

HRID 421573 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>[Cl:22][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:19])[C:9](=[O:10])[O:8][CH2:1][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-8436560834dd47ca93905e653bf50548
Source dataset
uspto-grants-2012_01
Patent number
US08101601B2

Reaction notes

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