Methyl iodide → HCID 13747414, compound

HRID 1587104Notes

Reaction equation

HRID 1587104 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:25]=[C:24]([CH2:26][C:27]([NH:29][CH:30]([C:43]([OH:45])=[O:44])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:28])[CH:23]=[CH:22][C:11]=1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:8].CI>CN(C)C=O>[CH2:7]([O:9][C:10]1[CH:25]=[C:24]([CH2:26][C:27]([NH:29][CH:30]([C:43]([O:45][CH3:1])=[O:44])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)=[O:28])[CH:23]=[CH:22][C:11]=1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13747425HCID 13747425, compound

Product 1

HCID 13747414HCID 13747414, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.28 g, 2 mmol) is added to a solution of benzyl 2-ethoxy-4-[N-(α-carboxy-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate (1.06 g, 2 mmol) in anhydrous dimethyl formamide (8 ml). The mixture is stirred for 10 minutes at ambient temperature, then methyl iodide (0.125 ml, 2 mmol) is added and the resulting mixture is stirred overnight at ambient temperature. It is filtered and the filtrate is concentrated by evaporation to dryness in vacuo. The evaporation residue is partitioned between aqueous sodium bicarbonate solution (pH=9) and methylene chloride. The organic phase was poured over sodium sulphate, filtered and concentrated by evaporation in vacuo. The evaporation residue is purified by column chromatography on silica gel (toluene/acetone=4/1) and crystallised from ether/petroleum ether.

Workup

  1. stirringthe resulting mixture is stirred overnight at ambient temperature
  2. filtrationIt is filtered
  3. concentrationthe filtrate is concentrated by evaporation to dryness in vacuo
  4. customThe evaporation residue is partitioned between aqueous sodium bicarbonate solution (pH=9) and methylene chloride
  5. additionThe organic phase was poured over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe evaporation residue is purified by column chromatography on silica gel (toluene/acetone=4/1)
  9. customcrystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-670aa2eb8c4b489c8e756db5da89f588
Source dataset
uspto-grants-1993_06
Patent number
US05216167

Reaction notes

Loading…