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Water → 5-Chloro-N-{[(5S)-3-{4-[3-{[(2-hydroxyethyl)amino]methyl}-2-oxopyridin-1(2H)-yl]-3-methyl-phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

HRID 85235
Notes
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Reaction equation

HRID 85235 reaction equation
N[CH:2]([OH:4])[CH3:3].Br[CH2:6][C:7]1[C:8](=[O:36])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26]([C:28]4[S:29][C:30]([Cl:33])=[CH:31][CH:32]=4)=[O:27])[O:21][C:20]3=[O:34])=[CH:15][C:14]=2[CH3:35])[CH:10]=[CH:11][CH:12]=1.O.C[N:39](C=O)C>>[Cl:33][C:30]1[S:29][C:28]([C:26]([NH:25][CH2:24][C@@H:22]2[O:21][C:20](=[O:34])[N:19]([C:16]3[CH:17]=[CH:18][C:13]([N:9]4[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][NH:39][CH2:3][CH2:2][OH:4])[C:8]4=[O:36])=[C:14]([CH3:35])[CH:15]=3)[CH2:23]2)=[O:27])=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 522583Acetaldehyde ammoniaHCID 59410175N-{[(5S)-3-{4-[3-(Bromomethyl)-2-oxopyridin-1(2H)-yl]-3-methylphenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}-5-chlorothiophene-2-carboxamide

Product 1

HCID 251516615-Chloro-N-{[(5S)-3-{4-[3-{[(2-hydroxyethyl)amino]methyl}-2-oxopyridin-1(2H)-yl]-3-methyl-phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

Procedure

At −10° C., 38 mg (0.63 mmol) of aminoethanol are added to a solution of 56 mg (0.11 mmol) of the compound from Example 11A in 1 ml of DMF. After 30 min at −10° C., the mixture is added to water and then extracted three times with ethyl acetate. The organic phases are combined and then freed from the solvent under reduced pressure. The product is purified by preparative HPLC using an acetonitrile/water mixture. This gives 14.5 mg (26% of theory) of the desired product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customThe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-e5c41719a1074ce286fce892844580d6
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes