Trifluoroacetic acid → (2E)-3-[6-(Methoxycarbonyl)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylic acid

HRID 82974Notes

Reaction equation

HRID 82974 reaction equation
C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[C:11]2[C:16](=[N:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:12]2)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:23][O:22][C:20]([CH:13]1[C:14](=[O:19])[NH:15][C:16]2[N:17]=[CH:18][C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])=[CH:10][C:11]=2[CH2:12]1)=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68338025Methyl 6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67154711(2E)-3-[6-(Methoxycarbonyl)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylic acidYield 107.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate (115 mg, 0.346 mmol; which may be prepared as described in Step 3) in DCM (693 μL) at 0° C. under Argon was added TFA (693 μL). The reaction was allowed to come back to room temperature under stirring for 2 h and then concentrated under vacuo to give the title compound (103 mg, quantitative) as a brown solid. The product was used without further purification.

Workup

  1. customto come back to room temperature
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-95f93e76bcd045e492bc0367ded59d35
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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