1,2-Dichloroethane → HCID 86601531, compound

HRID 1432523Notes

Reaction equation

HRID 1432523 reaction equation
[NH:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.[C:17]([NH:24][C@@H:25]([C:29](O)=[O:30])[CH:26]([CH3:28])[CH3:27])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(Cl)CCl>C(Cl)Cl>[C:17]([NH:24][C@@H:25]([C:29]([N:1]1[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6]1)=[O:30])[CH:26]([CH3:27])[CH3:28])([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 10176084Tetrahydropyridine3×

Product 1

HCID 86601531HCID 86601531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.245 g of tetrahydropyridine in 50 ml of CH2Cl2 are treated with 1.5 mmol per mmol of tetrahydropyridine of HOBT, 2.17 g of N-BOC-(R)-valin and 1.5 mmol per mmol of tetrahydropyridine of EDC and the mixture obtained is stirred at RT. From the mixture obtained solvent is evaporated, the evaporation residue obtained is mixed with EE and the mixture obtained is extracted with 0.1N HCl and saturated aqueous NaHCO3 solution. The organic phase obtained is dried and solvent is evaporated. N—(N-BOC-(R)-valyl-1,2,5,6-tetrahydropyridine is obtained.

Workup

  1. customthe mixture obtained
  2. customFrom the mixture obtained solvent
  3. customis evaporated
  4. customthe evaporation residue obtained
  5. additionis mixed with EE
  6. customthe mixture obtained
  7. extractionis extracted with 0.1N HCl and saturated aqueous NaHCO3 solution
  8. customThe organic phase obtained
  9. customis dried
  10. customsolvent is evaporated

Sources & evidence

ORD record
ord-75656e11af5648049dc3018db6604942
Source dataset
uspto-grants-2009_11
Patent number
US07612103B2

Reaction notes

Loading…