Acetic Acid → HCID 86726714, compound

HRID 1499477Notes

Reaction equation

HRID 1499477 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:24]([N+:25]([O-])=O)=[CH:23][N:22]=[C:21]3[C:16]=2[CH2:17][CH2:18][CH2:19][N:20]3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O>[Fe].O>[NH2:25][C:24]1[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10]2)=[C:16]2[C:21](=[N:22][CH:23]=1)[N:20]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:19][CH2:18][CH2:17]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86726713HCID 86726713, compound

Product 1

HCID 86726714HCID 86726714, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron powder (0.26 g, 4.6 mmol) was added to a mixture containing tert-butyl 5-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-nitro-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate (0.60 g, 1.2 mmol), AcOH (9 mL), and water (1 mL). The reaction mixture was stirred at room temperature for 2 h. The solution was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL) and filtered. The filtrate was neutralized with saturated aq. NaHCO3. The organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to give the sub-title compound (0.51 g, 90%). LCMS calc. for C23H38N5O4 (M+H)+: m/z=448.3. Found: 448.1.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (50 mL)
  4. filtrationfiltered
  5. washThe organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca53eb55451e4d5e9f6b82f9134b86b7
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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