m-Chloroperbenzoic acid → HCID 69480155, compound

HRID 2364284Notes

Reaction equation

HRID 2364284 reaction equation
FC1C=CC(CC2C=C3C(C(O)=C(C(OCC)=O)C(=[O:24])N3CCCSC)=NC=2)=CC=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]2[CH:48]=[C:47]3[C:42]([C:43]([OH:61])=[C:44]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[C:45](=[O:55])[N:46]3[CH2:49][CH2:50][CH2:51][S:52]([CH3:54])=[O:53])=[N:41][CH:40]=2)=[CH:34][CH:33]=1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]2[CH:48]=[C:47]3[C:42]([C:43]([OH:61])=[C:44]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[C:45](=[O:55])[N:46]3[CH2:49][CH2:50][CH2:51][S:52]([CH3:54])(=[O:24])=[O:53])=[N:41][CH:40]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 69480181HCID 69480181, compoundHCID 69480414HCID 69480414, compound

Product 1

HCID 69480155HCID 69480155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) solution of 30% ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylthio)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 70% ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (269 mg, 0.611 mmol) in dichloromethane (10 mL) was added m-chloroperoxybenzoic acid (158 mg, 0.915 mmol). The reaction mixture was warmed to room temperature and stirred 3 hours. The reaction mixture was diluted with dichloromethane and washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfonyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1 H), 7.66 (s, 1 H), 7.22 (dd, J=8.5, 5.5 Hz, 2 H), 7.03 (t, J=8.5 Hz, 2 H), 4.52 (q, J=7.1 Hz, 2 H), 4.39 (t, J=7.8 Hz, 2 H), 4.13 (s, 2 H), 3.16 (t, J=6.9 Hz, 2 H), 2.95 (s, 3 H), 2.22 (m, 2 H), 1.48 (t, J=7.0 Hz, 3 H); MS m/z 461 (M−H)−.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-68af334bb8344527a0fdcf4bcefd58be
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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