Methyl bromide acetonitrile → (3S)-3-({({(2R)-1-({(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-2-pyrrolidinyl}carbonyl)-2-pyrrolidinyl}carbonyl)amino}methyl)-1,1-dimethylpiperidinium bromide

HRID 272089Notes

Reaction equation

HRID 272089 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@@H:40]2[CH2:45][CH2:44][CH2:43][N:42]([CH3:46])[CH2:41]2)=[O:37])=[O:30])[CH2:3]1.C[Br:48].[C:49](#N)C>>[Br-:48].[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@@H:40]2[CH2:45][CH2:44][CH2:43][N+:42]([CH3:49])([CH3:46])[CH2:41]2)=[O:37])=[O:30])[CH2:3]1

Participants

3

Reactant 2

HCID 22594519Methyl bromide acetonitrileHCID 69100833(2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-{((3S)-1-methyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide

Product 1

HCID 69101449(3S)-3-({({(2R)-1-({(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)-2-pyrrolidinyl}carbonyl)-2-pyrrolidinyl}carbonyl)amino}methyl)-1,1-dimethylpiperidinium bromide

Procedure

To 15 mg of (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-{((3S)-1-methyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide, 0.5 ml of 10% methyl bromide-acetonitrile was added at room temperature, followed by 12 hours' stirring. The solvent in the reaction liquid was distilled off under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography (aluminium oxide 60F254, Art. 5713 (Merck), choroform/methanol=18/1) to provide 15 mg of the title compound as a white solid.

Workup

  1. customThe solvent in the reaction liquid
  2. distillationwas distilled off under reduced pressure
  3. customthe resulting residue was purified by preparative thin-layer chromatography (aluminium oxide 60F254, Art. 5713 (Merck), choroform/methanol=18/1)

Sources & evidence

ORD record
ord-654423ce16344b95b39d50fcd0af939a
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

Loading…