Water → HCID 86626076, compound

HRID 390597Notes

Reaction equation

HRID 390597 reaction equation
FC(F)(F)C(O)=O.C(OC([CH2:15][NH:16][C:17]1[CH:18]=[C:19]([C:23]2[N:28]=[CH:27][C:26](/[CH:29]=[C:30](\[O:36][CH2:37][CH3:38])/[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)=O)(C)(C)C.O>ClCCl>[CH2:37]([O:36]/[C:30](=[CH:29]\[C:26]1[CH:27]=[N:28][C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([NH:16][CH3:15])[CH:18]=2)=[CH:24][CH:25]=1)/[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:38]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86626077HCID 86626077, compound

Product 1

HCID 86626076HCID 86626076, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.62 mL (7.0 mmol) of trifluoroacetic acid is added to a solution of 0.30 g (0.7 mmol) of ethyl (Z)-3-{6-[3-(tert-butoxycarbonylmethylamino)phenyl]pyrid-3-yl}-2-ethoxyacrylate in 10 mL of dichloromethane. The reaction mixture is stirred at room temperature for 20 hours. The reaction is stopped by addition of 10 mL of water and extraction with dichloromethane. The organic phases are combined and then dried over magnesium sulfate. After filtration, the solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture to give 0.19 g (86%) of ethyl (Z)-2-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]acrylate in the form of a yellow solid.

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationAfter filtration
  3. customthe solvents are evaporated off
  4. customThe crude product obtained
  5. customis purified by chromatography on a column of silica
  6. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-0825cd0529a14d26a854428f368966ac
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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