Dichloromethane → Ethyl α-ethoxy-6-[3-(methylamino)phenyl]-3-pyridinepropanoate

HRID 2426338Notes

Reaction equation

HRID 2426338 reaction equation
C(OC([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:16]2[N:21]=[CH:20][C:19]([CH2:22][CH:23]([O:29][CH2:30][CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=2)[CH:13]=[CH:14][CH:15]=1)=O)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>O>[CH2:30]([O:29][CH:23]([CH2:22][C:19]1[CH:20]=[N:21][C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][CH3:8])[CH:11]=2)=[CH:17][CH:18]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:31]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67148315HCID 67148315, compound

Product 1

HCID 67148466Ethyl α-ethoxy-6-[3-(methylamino)phenyl]-3-pyridinepropanoateYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.11 g (0.3 mmol) of ethyl 3-{6-[3-(tert-butoxycarbonylmethylamino)phenyl]pyrid-3-yl}-2-ethoxypropanoate, 5 ml of dichloromethane and 0.15 ml (1.9 mmol) of trifluoroacetic acid are stirred at room temperature for 24 hours. After addition of water, the reaction medium is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and evaporated. 80 mg (94%) of ethyl 2-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]propanoate are obtained.

Workup

  1. extractionthe reaction medium is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1796e700de47498288e475adf12e568c
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

Loading…