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

HRID 1532850Notes

Reaction equation

HRID 1532850 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-d959dea90f2b4563bceaa561665ce9a1
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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