Chloromethyl Methyl Ether → HCID 86748548, compound

HRID 1608669Notes

Reaction equation

HRID 1608669 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[C@H:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:10]([C:16]([OH:18])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][CH2:36]Cl>CN(C)C=O.C(OCC)(=O)C>[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[C@H:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:10]([C:16]([O:18][CH2:34][O:35][CH3:36])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 70340536HCID 70340536, compound

Product 1

HCID 86748548HCID 86748548, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 mg of (4R)-5-(2-cyanoethoxycarbonyl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid in 0.5 ml of N,N-dimethylformamide were added 4.3 mg of potassium carbonate, and then 8 μl of chloromethyl methyl ether. The mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with 5 ml of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and with water, and dried over anhydrous Glauber's salt (sodium sulfate), followed by distilling off the solvent under reduced pressure the residue was purified using preparative TLC to obtain 3.6 mg of the objective compound.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and with water
  2. dry with materialdried over anhydrous Glauber's salt (sodium sulfate)
  3. distillationby distilling off the solvent under reduced pressure the residue
  4. customwas purified

Sources & evidence

ORD record
ord-b1ca48c26ce943f597081255d5c2922f
Source dataset
uspto-grants-1995_03
Patent number
US05395941

Reaction notes

Loading…