HCID 118863127, compound → HCID 118863120, compound

HRID 63924Notes

Reaction equation

HRID 63924 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[O:17])[CH:8]([C:14]#[N:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[NH2:15][C:14]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

3

Reactant 1

HCID 118863127HCID 118863127, compound

Product 1

HCID 118863120HCID 118863120, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 3-(4-chlorobenzyl)-4-(3-chlorophenyl)-2-cyano-4-oxobutanoate (1.945 g, 5 mmol) in TFA (20 mL) was stirred at 100° C. for 3 h. The reaction was cooled to RT and concentrated to a residue which was diluted with EA (40 mL) and water (8 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1) to give ethyl 2-amino-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (1.4 g, 72% yield) as a white solid. LCMS: MH+ 390 and TR=2.503 min.

Workup

  1. concentrationconcentrated to a residue which
  2. additionwas diluted with EA (40 mL) and water (8 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by chromatography
  6. washeluted with PE/EA (5:1)

Sources & evidence

ORD record
ord-4d6a4acf74c24c118cdab15f3f3a756d
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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