Methyl iodide → HCID 60209115, compound

HRID 1095392Notes

Reaction equation

HRID 1095392 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C@H:3]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1[N:5]=[N:6][NH:7][N:8]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:1][C:2]([CH3:21])([CH3:20])[C@H:3]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1[N:5]=[N:6][N:7]([CH3:22])[N:8]=1.[CH3:1][C:2]([CH3:21])([CH3:20])[C@H:3]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]1[N:8]([CH3:22])[N:7]=[N:6][N:5]=1

Participants

6

Reactant 3

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

Product 2

HCID 60209114HCID 60209114, compoundYield 28%HCID 60209115HCID 60209115, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of benzyl [(1S)-2,2-dimethyl-1-(2H-tetrazol-5-yl)propyl]carbamate (280 mg, 0.96 mmol), potassium carbonate (660 mg, 4.8 mmol) and methyl iodide (0.24 mL, 3.8 mmol) in acetone (5 mL) was stirred at 0° C. for 10 min and warmed to rt. After 4 h, the 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 166 mg (57%) of benzyl [(1S)-2,2-dimethyl-1-(2-methyl-2H-tetrazol-5-yl)propyl]carbamate and 82 mg (28%) of benzyl [(1S)-2,2-dimethyl-1-(1-methyl-1H-tetrazol-5-yl)propyl]carbamate.

Workup

  1. temperaturewarmed to rt
  2. waitAfter 4 h
  3. filtrationthe 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-6f43f1a636a24693b4c715731c785324
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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