HCID 59612108, compound → HCID 59612116, compound

HRID 1907122Notes

Reaction equation

HRID 1907122 reaction equation
[CH2:1]([O:3][C:4](=[O:20])/[C:5](/[NH2:19])=[CH:6]/[C:7](=[O:18])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[F:17])[CH3:2]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:5]1[NH:19][CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[F:17])[CH2:8][C:7](=[O:18])[CH:6]=1)=[O:20])[CH3:2]

Participants

3

Reactant 1

HCID 59612108HCID 59612108, compound

Product 1

HCID 59612116HCID 59612116, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example 5, (2Z,5E)-2-amino-6-(4-chloro-2-fluoro-phenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester (7; 88 g, 0.296 mol) in 1,4-dioxane (880 mL) in a 2 liter Parr reactor gave, following purification by silica gel chromatography eluting with 40% EtOAc/hexanes, 6-(4-chloro-2-fluorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (11; 43 g, 49%, 96% pure by HPLC) as a tan solid.

Workup

  1. customgave
  2. custompurification by silica gel chromatography
  3. washeluting with 40% EtOAc/hexanes, 6-(4-chloro-2-fluorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (11; 43 g, 49%, 96% pure by HPLC) as a tan solid

Sources & evidence

ORD record
ord-841e96a94c6740dd945dcd91b575c408
Source dataset
uspto-grants-2013_12
Patent number
US08598086B2

Reaction notes

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