HCID 70248930, compound → HCID 69893148, compound

HRID 2120066Notes

Reaction equation

HRID 2120066 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][C:5]([NH:7][CH:8]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:6]>CCO>[ClH:1].[ClH:1].[NH2:3][CH2:4][C:5]([NH:7][CH:8]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:6].[ClH:1].[ClH:1].[NH2:7][CH:8]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 70248930HCID 70248930, compound

Product 2

HCID 69893148HCID 69893148, compoundHCID 70248930HCID 70248930, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

DL-3-amino-3-(3-pyridyl)propionic acid (220 g) from Step 1 was slurried in absolute EtOH (3.6 liters). HCl gas (one lecture bottle -lb) was bubbled into the reaction while stirring over 40 minutes. The slurry was then heated at reflux for 4 hours (a solution forms after 1 to 1.5 hours). The reaction mixture was cooled to 5° C. in an ice bath. After stirring at 5° C. for 1.5 hours, the resulting white precipitate was filtered and washed thoroughly with ether. After drying under vacuum at 50° C., the desired product, ethyl DL-3-amino-3-(3-pyridyl)propionate dihydrochloride was obtained as a white solid (331.3 g).

Workup

  1. customHCl gas (one lecture bottle -lb) was bubbled into the reaction
  2. temperatureThe slurry was then heated
  3. temperatureat reflux for 4 hours (a solution forms after 1 to 1.5 hours)
  4. stirringAfter stirring at 5° C. for 1.5 hours
  5. filtrationthe resulting white precipitate was filtered
  6. washwashed thoroughly with ether
  7. customAfter drying under vacuum at 50° C.

Sources & evidence

ORD record
ord-c27e19521e8d48a4b42b8cd8565ea9ba
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

Loading…