Chloromethyl Methyl Ether → HCID 86699049, compound

HRID 1424189Notes

Reaction equation

HRID 1424189 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][CH3:12])[NH:7][C:6]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][CH2:30]Cl>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:11][CH3:12])[N:7]([CH2:28][O:29][CH3:30])[C:6]=2[CH:21]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 86699047HCID 86699047, compound

Product 1

HCID 86699049HCID 86699049, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl (1-(6-bromo-1H-benzo[d]imidazol-2-yl)propyl)carbamate (Preparation 18, 0.97 g, 2.7 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (1.35 g, 9.77 mmol) and chloromethyl methyl ether (0.40 mL, 5.3 mmol), and the reaction was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (580 mg, 53%) as a white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 0-100% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-d9e60559cb8e499285924e06f89df41f
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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