Water → HCID 21699687, compound

HRID 1597278Notes

Reaction equation

HRID 1597278 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([C:22]([OH:24])=[O:23])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]3=[C:11]([C:22]([O:24][CH3:25])=[O:23])[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21699693HCID 21699693, compound

Product 1

HCID 21699687HCID 21699687, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine-10-carboxylic acid (500 mg, 1.523 mmol) was dissolved in N,N-dimethylformamide (3 ml), followed by adding thereto potassium carbonate (315.1 mg, 2.28 mmol) and methyl iodide (0.13 ml, 2.06 mmol), and the resulting mixture was stirred overnight at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the desired compound (487 mg, 93.4%) as a brown oil.

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-7dbeee8ac6fe408c92842b1b53e43a7c
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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