Triethylamine → {3-[4-(4-Chloro-benzoylamino)-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester

HRID 885381Notes

Reaction equation

HRID 885381 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH2:22][N:23]2[CH2:27][CH2:26][O:25][C:24]2=[O:28])[CH:7]=1)[CH3:2].[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:31]([Cl:30])=[CH:32][CH:33]=3)=[CH:17][C:16]=2[CH2:22][N:23]2[CH2:27][CH2:26][O:25][C:24]2=[O:28])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 58237507{3-[4-Amino-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester

Product 1

HCID 58237496{3-[4-(4-Chloro-benzoylamino)-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{3-[4-Amino-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester (0.15 g, 0.38 mmol), 4-chlorobenzoyl chloride (0.15 g, 0.86 mmol), and triethylamine (0.27 mL, 1.9 mmol) were combined in CH2Cl2 (10 mL) and stirred at room temperature until no starting material was seen by analytical tlc. The mixture was concentrated to give the title compound, which was used directly in the hydrolysis step.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-6a552d9dc0a840db935d5b3d067ab21b
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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