Trifluoroacetic acid → HCID 90073736, compound

HRID 1410825Notes

Reaction equation

HRID 1410825 reaction equation
C([O:5][C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[CH:16][C:17]2[C:18](=[O:32])[N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])(C)(C)C.[F:34][C:35]([F:40])([F:39])C(O)=O>C(Cl)Cl>[F:34][C:35]([F:40])([F:39])[C:6]([NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[CH:16][C:17]2[C:18](=[O:32])[N:19]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68297412HCID 68297412, compound

Product 1

HCID 90073736HCID 90073736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{3-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester (27 mg, 0.060 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (1 mL) was added, and the mixture was stirred at r.t. for 1 h. Solvent and excess TFA were removed in vacuo. To the residue were added THF (3 mL), triethylamine (0.050 mL), and ethyl trifluoroacetate (2 mL), and the resulting mixture was refluxed for 16 h. After cooling to r.t., mixture was concentrated to dryness. 0.1 M HCl and EtOAc were added, and the aqueous layer was extracted with additional EtOAc. The organic layers were combined, dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 16.4 mg of the title compound as a pale yellow solid. MS: (+) m/z 449.23 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. additionTo the residue were added THF (3 mL), triethylamine (0.050 mL), and ethyl trifluoroacetate (2 mL)
  3. temperaturethe resulting mixture was refluxed for 16 h
  4. temperatureAfter cooling to r.t.
  5. concentrationmixture was concentrated to dryness
  6. addition0.1 M HCl and EtOAc were added
  7. extractionthe aqueous layer was extracted with additional EtOAc
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9c2041b91ceb4dde943871e3a6881631
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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