Methyl iodide → HCID 60209115, compound

HRID 1095399Notes

Reaction equation

HRID 1095399 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[NH:10][C@H:11]([C:16]1[N:17]=[N:18][NH:19][N:20]=1)[C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([O:8][C:9](=[O:21])[NH:10][C@H:11]([C:16]1[N:20]=[N:19][N:18]([CH3:22])[N:17]=1)[C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57463446HCID 57463446, compound

Product 1

HCID 60209115HCID 60209115, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of benzyl[(1S)-2,2-dimethyl-1-(2H-tetrazol-5-yl)propyl]carbamate (0.41 g, 1.4 mmol), potassium carbonate (1.0 g, 7.0 mmol) and methyl iodide (0.35 mL, 5.6 mmol) in acetone (7 mL) was stirred at 0° C. for 10 min and warmed to rt. After 5 h, the reaction mixture was filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (8/1-4/1-1/1) to afford 0.29 g (68%) of the title compound.

Workup

  1. temperaturewarmed to rt
  2. waitAfter 5 h
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (8/1-4/1-1/1)

Sources & evidence

ORD record
ord-84233dd402ca4fc1bd62d45b6a22ffcb
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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