Methyl iodide → HCID 11348311, compound

HRID 1374423Notes

Reaction equation

HRID 1374423 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22][OH:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]I>C(#N)C.[Ag]=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22][O:23][CH3:24])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 15043091HCID 15043091, compound

Product 1

HCID 11348311HCID 11348311, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate (4.0 g, 12.4 mmol) in acetonitrile (80 ml) were added silveroxide (14.3 g, 61.7 mmol) and methyliodide (7.7 ml, 124 mmol), and the mixture was stirred for 19 hours. After removal of the insoluble materials, the solvent was removed in vacuo and the residue was purified with silica gel chromatography to give tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-methoxypentanoate (2.98 g, 71%).

Workup

  1. customAfter removal of the insoluble materials
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-c74257373f7041299672e9a930d1814e
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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