3-(Chloromethyl)pyridine hydrochloride → 4-(3-Pyridylmethoxymethylene)-2-phenylbenzoylmethionine methyl ester

HRID 325224Notes

Reaction equation

HRID 325224 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].Cl.Cl[CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>CS(C)=O.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10](=[CH:13][O:14][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 20622833[4-Hydroxymethyl-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 675506094-(3-Pyridylmethoxymethylene)-2-phenylbenzoylmethionine methyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The resultant compound from Example 16D (1.0 equivalent) is treated with sodium hydride (2.0 equivalents) in DMSO, then 3-chloromethylpyridine hydrochloride (1.0 equivalent) is added. When judged complete by TLC analysis, the reaction is diluted with water and ethyl acetate, the organic layer is dried and concentrated, and the crude title compound is purified by chromatography on silica gel.

Workup

  1. customthe organic layer is dried
  2. concentrationconcentrated
  3. customthe crude title compound is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c25dc9b17df448eea8f96a3f10b1e795
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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