Methyl iodide → Boc-Chg-Ome

HRID 2242438Notes

Reaction equation

HRID 2242438 reaction equation
[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:9]([OH:11])=[O:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:19]I.[Al]>CC(C)=O.[Ag-]=O>[CH3:19][O:10][C:9](=[O:11])[C@@H:2]([NH:1][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5359268AluminumHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycine

Product 1

HCID 13773589Boc-Chg-OmeYield 100.2%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of Boc-Chg-OH (53 mg, 0.206 mmol) in acetone (3 mL) were added methyl iodide (195 μL, 3.1 mmol) and silver (I) oxide (53 mg, 0.229 mmol). The mixture was allowed to stir over night in a reaction flask that was covered with aluminium foil. Thereafter the solution was filtered through celite and evaporated. Purification by flash column chromatography (toluene/ethyl acetate 15:1) provided methyl ester 54 (56 mg, 100%) as a colorless oil.

Workup

  1. filtrationThereafter the solution was filtered through celite
  2. customevaporated
  3. customPurification by flash column chromatography (toluene/ethyl acetate 15:1)

Sources & evidence

ORD record
ord-27393fcdb616489db3315c6d4915d2d1
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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