Methyl iodide → HCID 67079752, compound

HRID 655534Notes

Reaction equation

HRID 655534 reaction equation
I[CH3:2].[C:3]([O:7][C:8](=[O:23])[NH:9][C@H:10]([CH2:21][OH:22])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:6])([CH3:5])[CH3:4]>CN(C)C=O.[Ag-]=O>[C:3]([O:7][C:8](=[O:23])[NH:9][C@H:10]([CH2:21][O:22][CH3:2])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH3:5])([CH3:4])[CH3:6]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 67080097HCID 67080097, compound

Product 1

HCID 67079752HCID 67079752, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Silver(I) oxide (4.49 g, 19.4 mmol) and iodomethane (2.75 g, 19.4 mmol) were added at room temperature to a solution or ((S)-3-benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester (2.60 g, 8.81 mmol) in N,N-dimethylformamide (8 mL). The reaction mixture was heated at 40° C. for 2.5 h, then insoluble material was removed by filtration through diatomaceous earth. After evaporation of the filtrate, the residue was taken up in ethyl acetate and washed with water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (2.72 g, 100%), which was used without further purification. Colorless liquid, MS (ISP)=310.3 (M+H)+.

Workup

  1. custominsoluble material was removed by filtration through diatomaceous earth
  2. customAfter evaporation of the filtrate
  3. washwashed with water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e290fa07314547029a1d9b6f0f115abb
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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