Methyl iodide → HCID 89852975, compound

HRID 627110Notes

Reaction equation

HRID 627110 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([C:16]([CH3:18])=[CH2:17])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3].[CH3:19]I.[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([C:16]([CH3:18])=[CH2:17])=[CH:8][C@H:9]2[CH2:14][O:15][CH3:19])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89852119HCID 89852119, compound2×

Product 1

HCID 89852975HCID 89852975, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-4-(prop-1-en-2-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 58, 0.289 g, 1.15 mmol) in DMF (10 mL) at 0° C. was added methyl iodide (0.435 mL, 6.93 mmol) followed by sodium hydride (60% in mineral oil) (0.051 g, 1.27 mmol). The reaction was stirred for 1.5 hours at 0° C. The reaction mixture was diluted with ethyl acetate and washed twice with water. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-50% ethyl acetate/hexanes) afforded the desired product as a pale yellow oil (233 mg, 76%).

Workup

  1. washwashed twice with water
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5274703ad9f47e094815b98feba5581
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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