Methyl iodide → HCID 66652988, compound

HRID 572567Notes

Reaction equation

HRID 572567 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH:9]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=1[F:27])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:6])([CH3:5])[CH3:4].[CH3:28]I>CN(C=O)C>[C:3]([O:7][CH2:8][CH:9]([N:17]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=1[F:27])[CH3:28])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66652717HCID 66652717, compound

Product 1

HCID 66652988HCID 66652988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (1.8 g, 0.038 mol) in dry DMF (10 mL) at 0° C., tert-butyl 3-tert-butoxy-2-[(4-cyano-2-fluorobenzyl)amino]propanoate (6.7 g, 0.019 mol) in DMF (20 mL) was added dropwise. The resulting mixture was allowed to stir for 20 min at RT. Methyl iodide (3.5 mL, 0.0057 mol) was then added dropwise at 000 and the mixture was allowed to stir for 3 hr at RT. The reaction mixture was quenched in ice water and extracted with ethyl acetate (250 mL). The organic layer was washed with water (3×100 mL), dried over sodium sulphate and concentrated under reduced pressure. The crude was purified by column chromatography using petroleum ether and ethyl acetate as eluent, affording the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (d, J=9.8 Hz, 1H), 7.67 (t, J=2.5 Hz, 2H), 3.92 (d, J=15.2 Hz, 1H), 3.81-3.70 (d, J=15.0 Hz, 1H), 3.63 (m, 1H), 3.52 (m, 2H), 2.26 (s, 3H), 1.42 (s, 9H), 1.08 (s, 9H).

Workup

  1. stirringto stir for 3 hr at RT
  2. customThe reaction mixture was quenched in ice water
  3. extractionextracted with ethyl acetate (250 mL)
  4. washThe organic layer was washed with water (3×100 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-4c5196d447c349078d5ad9e2dfc81101
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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