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

HRID 383095Notes

Reaction equation

HRID 383095 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-e197e3edd89a4d7984f203657e85cb66
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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