Triethylamine → {4-[(3-Sulfonylmethylpyridyl)amino]-2-phenylbenzoyl}methionine methyl ester

HRID 383109Notes

Reaction equation

HRID 383109 reaction equation
Cl.Cl[S:3]([CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:4].[CH3:13][O:14][C:15](=[O:37])[C@H:16]([CH2:33][CH2:34][S:35][CH3:36])[NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:13][O:14][C:15](=[O:37])[C@H:16]([CH2:33][CH2:34][S:35][CH3:36])[NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:8]2[C:7]([CH:6]=[S:3](=[O:5])=[O:4])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:21][C:20]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl esterHCID 23436466(Pyridin-3-yl)methanesulfonyl chloride hydrochloride

Product 1

HCID 20622808{4-[(3-Sulfonylmethylpyridyl)amino]-2-phenylbenzoyl}methionine methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chlorosulfonylmethylpyridine hydrochloride (1.0 equivalent) and (4-amino-2-phenylbenzoyl)methionine methyl ester (1.0 equivalent) in dichloromethane is treated with triethylamine (2.2 equivalents). When judged complete by TLC analysis, the reaction is diluted with ethyl acetate, and then is washed with pH 4 water, saturated NaHCO3, and brine. The mixture is dried and concentrated to give the crude title compound which is purified by chromatography on silica gel.

Workup

  1. washis washed with pH 4 water, saturated NaHCO3, and brine
  2. customThe mixture is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-753de4411cfc4a03abc9b6b55d521676
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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