Thionyl Chloride → HCID 59548993, compound

HRID 421575Notes

Reaction equation

HRID 421575 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[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:30])=O>ClCCl>[Cl:30][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[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 66674096HCID 66674096, compound

Product 1

HCID 59548993HCID 59548993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.6 g (15 mmol) of the 5-{[(benzyloxy)carbonyl](4-methoxybenzyl)amino}valeric acid obtained in this way are dissolved in 60 ml of dichloromethane, and 2.2 ml of thionyl chloride are added. The mixture is heated under reflux for 30 min. 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. 5.7 g (98% 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 30 min
  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. custom5.7 g (98% of theory) of the target compound are obtained
  8. customare reacted further without further purification and characterization

Sources & evidence

ORD record
ord-65b0c2237d9546279834951ad35b5f61
Source dataset
uspto-grants-2012_01
Patent number
US08101601B2

Reaction notes

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