Trifluoroacetic acid → 1-{[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid

HRID 1410769Notes

Reaction equation

HRID 1410769 reaction equation
C([O:5][C:6]([C:8]1([CH2:12][NH:13][C:14]([C:16]2[N:17]=[C:18]([C:35]#[N:36])[C:19]3[C:20](=[O:34])[N:21]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=[CH:23][C:24]=3[C:25]=2[OH:26])=[O:15])[CH2:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:27]([N:21]1[C:20](=[O:34])[C:19]2[C:18]([C:35]#[N:36])=[N:17][C:16]([C:14]([NH:13][CH2:12][C:8]3([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][CH2:11]3)=[O:15])=[C:25]([OH:26])[C:24]=2[CH:23]=[CH:22]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 682974431-{[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl ester

Product 1

HCID 682974731-{[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{[(7-Benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl ester (32 mg, 0.066 mmol) was dissolved in 2 mL of CH2Cl2. Trifluoroacetic acid (0.4 mL) was added, and the mixture was stirred at r.t. for 2 h. The mixture was concentrated in vacuo, and the residue was dissolved in saturated NaHCO3. The aqueous solution was washed with ether, and then acidified to pH about 1 with 4 M HCl to give a white suspension. The solid was isolated by filtration and dried under vacuum to give 22 mg of the title compound as an off-white solid. MS: (+) m/z 433.35 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in saturated NaHCO3
  3. washThe aqueous solution was washed with ether
  4. customto give a white suspension
  5. customThe solid was isolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-132a36fc6a184ea3b11ae851c0264ba1
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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