Methyl iodide → HCID 57905225, compound

HRID 1093112Notes

Reaction equation

HRID 1093112 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:14]([C:15](=[O:25])[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][CH:12]1[CH2:26][CH2:27][C:9]2([O:28][CH2:29][CH2:30][OH:31])[CH2:10][CH2:11]1)=[O:5])C.[H-].[Na+].[CH3:34]I>CN(C=O)C>[CH3:1][O:3][C:4]([C:6]1[N:7]=[C:8]2[N:14]([C:15](=[O:25])[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][CH:12]1[CH2:26][CH2:27][C:9]2([O:28][CH2:29][CH2:30][O:31][CH3:34])[CH2:10][CH2:11]1)=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57904839HCID 57904839, compound

Product 1

HCID 57905225HCID 57905225, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzyloxy-1-(2-hydroxy-ethoxy)-6-oxo-3,7-diazatricyclo[7.2.2.02,7]trideca-2,4-diene-4-carboxylic acid ethyl ester (105 mg, 0.245 mmol) in DMF (1 mL) was added 60% NaH (15 mg, 0.37 mmol) and the mixture stirred at room temp. for 15 min. under N2. After H2 gas evolution had ceased, MeI (0.031 mL, 0.490 mmol) was added and the mixture stirred at room temperature overnight. The mixture was concentrated and the residue was taken up in ethyl acetate (10 mL), washed with water followed by brine, then dried (Na2SO4) and concentrated to provide 85 mg of a crude oil which was purified by C-18 reverse phase column chromatography (YMC AQ, 18-22-26-30-34% CH3CN/H2O with 01% trifluoroacetic acid) to provide 8 mg (0.019 mmol, 8% yield) of the title compound as an amber film: HPLC: retention time=2.30 min (area percent=91%); LC/MS: m/z 429 (M+H); 1H NMR (500 MHz, CDCl3) δ ppm 1.66-1.70 (2H, m), 1.87-2.02 (2H, m), 2.12 (4H, t, J=7.5 Hz), 2.46 (1H, brs), 3.39 (3H, s), 3.62 (2H, t, J=4.7 Hz), 3.73 (2H, d, J=4.7 Hz), 3.84 (3H, s), 4.07 (2H, d, J=3.7 Hz), 5.26 (2H, s), 7.31 (1H, t, J=7.0 Hz), 7.36 (2H, t, J=7.3 Hz), 7.48 (2H, d, J=7.6 Hz).

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe mixture was concentrated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto provide 85 mg of a crude oil which
  7. customwas purified by C-18 reverse phase column chromatography (YMC AQ, 18-22-26-30-34% CH3CN/H2O with 01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6bfa3013ed90471a864a4d82060bf9b0
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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