Chloroform → n-((5s)-3-(4-(1-Formyl-2s-(pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

HRID 395568Notes

Reaction equation

HRID 395568 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][NH:10]1.C(Cl)(Cl)Cl.ClCCl.[CH:38](OCC)=[O:39]>>[CH:38]([N:10]1[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)=[CH:13][CH:9]1[CH2:8][S:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:39]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6344DichloromethaneHCID 8025Ethyl formateHCID 69998857n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Product 1

HCID 88095554n-((5s)-3-(4-(1-Formyl-2s-(pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamideYield 20%

Procedure

The amine (Reference Example 7, 0.048 g, 0.11 mM) was refluxed in ethyl formate (3 ml). After 2 hours, chloroform (1 ml) and dichloromethane (1 ml) was added to solublise the precipitate. After 70 hours the solution was evaporated and the residue dissolved in acetonitrile/EtOAc (1:1) and the precipitate removed by filtration. The mother liquor was purified by Isolute chromatography (using as eluant a mixture increasing in polarity from 50% to 70% MeCN in EtOAc) to give after trituration with diethyl ether the title product (0.010 g, 20%).

Workup

  1. customAfter 70 hours the solution was evaporated
  2. dissolutionthe residue dissolved in acetonitrile/EtOAc (1:1)
  3. customthe precipitate removed by filtration
  4. customThe mother liquor was purified by Isolute chromatography (
  5. temperatureincreasing in polarity from 50% to 70% MeCN in EtOAc)

Sources & evidence

ORD record
ord-7446e6d16f404f23a3bbfea95e7a722c
Source dataset
uspto-grants-2003_08
Patent number
US06605630B1

Reaction notes

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