Trifluoroacetic acid → 3-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid

HRID 919832Notes

Reaction equation

HRID 919832 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:46])[C:14]([CH3:45])([CH3:44])[CH2:15][NH:16][C:17]([C:19]1[C:20]([OH:43])=[C:21]2[C:26](=[CH:27][N:28]=1)[N:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24](=[O:36])[C:23]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[CH:22]2)=[O:18])(C)(C)C>C(Cl)Cl>[CH2:29]([N:25]1[C:26]2[C:21](=[C:20]([OH:43])[C:19]([C:17]([NH:16][CH2:15][C:14]([CH3:45])([CH3:44])[C:13]([OH:46])=[O:12])=[O:18])=[N:28][CH:27]=2)[CH:22]=[C:23]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:24]1=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 682976033-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester

Product 1

HCID 682971863-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acidYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a mixture of 3-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester (22 mg, 0.042 mmol) and CH2Cl2 (3 mL), and the resulting mixture was stirred for 2 h. Solvent was evaporated in vacuo, and the residue was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 2 and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 11.8 mg of the title compound as a light yellow solid. MS: (+) m/z 472.34 (M+1).

Workup

  1. customSolvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in saturated NaHCO3
  3. washwashed several times with ether
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-07b7bd70ae00401ab301c5750fca1565
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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