Ethyl Acetate → 1-(2,4-Dimethoxybenzyl)-3-(3-fluorobenzyl)-1-(4-((2-oxooxazolidin-3-yl)methyl)thiazol-2-yl)urea

HRID 1685087Notes

Reaction equation

HRID 1685087 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([N:8]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[O:10])[S:6][CH:7]=1.[O:31]1[CH2:35][CH2:34][NH:33][C:32]1=[O:36].[H-].[Na+].CCOC(C)=O>CN(C=O)C>[CH3:30][O:29][C:22]1[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=1[CH2:20][N:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:33]2[CH2:34][CH2:35][O:31][C:32]2=[O:36])[N:4]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 580550941-(4-(Chloromethyl)thiazol-2-yl)-1-(2,4-dimethoxybenzyl)-3-(3-fluorobenzyl)urea2×

Product 1

HCID 580550571-(2,4-Dimethoxybenzyl)-3-(3-fluorobenzyl)-1-(4-((2-oxooxazolidin-3-yl)methyl)thiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-(4-Chloromethyl-thiazol-2-yl)-1-(2,4-dimethoxy-benzyl)-3-(3-fluoro-benzyl)-urea (Intermediate 21, 0.3 mmol) was taken up in DMF (2 ml). A solution of the oxazolidin-2-one (or sultam) (1 eq.) with NaH (1 eq.) in DMF (2 ml) was added. The reaction was allowed to stir at room temperature for 2 hours. An aqueous workup with EtOAc was performed. Purified by column chromatography using a gradient of 0-100% EtOAc/hexanes to give 1-(2,4-dimethoxybenzyl)-3-(3-fluorobenzyl)-1-(4-((2-oxooxazolidin-3-yl)methyl)thiazol-2-yl)urea.

Workup

  1. customPurified by column chromatography

Sources & evidence

ORD record
ord-cf0429ae297641b4968c9e49d3b69526
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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