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

HRID 910324Notes

Reaction equation

HRID 910324 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-556e47dd99204d00a4c2072b59d6e43e
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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