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

HRID 1864576Notes

Reaction equation

HRID 1864576 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-0e5f06bfdc90427d841f315dd72bdcd2
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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