Triethylamine → 5-{2,6-difluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}piperidin-2-one

HRID 10833Notes

Reaction equation

HRID 10833 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([CH:16]3[CH2:21][NH:20][C:19](=[O:22])[CH2:18][CH2:17]3)=[C:11]([F:23])[CH:10]=2)[CH2:4]1.FC1C=C(N2C[C@H](CNC(=O)C)OC2=O)C=C(F)C=1I.CCN(CC)CC.Cl[CH:52](Cl)/[CH:53]=[N:54]/[NH:55]S(C1C=CC(C)=CC=1)(=O)=O>CO>[F:23][C:11]1[CH:10]=[C:9]([N:5]2[CH2:4][C@H:3]([CH2:2][N:1]3[CH:52]=[CH:53][N:54]=[N:55]3)[O:7][C:6]2=[O:8])[CH:14]=[C:13]([F:15])[C:12]=1[CH:16]1[CH2:21][NH:20][C:19](=[O:22])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10869706N-[(E)-2,2-dichloroethylideneamino]-4-methylbenzenesulfonamideHCID 54435806(S)-N-[[3-(4-iodo-3,5-difluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamideHCID 695581245-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl}piperidin-2-one

Product 1

HCID 100224555-{2,6-difluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}piperidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl}piperidin-2-one (0.1 g, 0.31 mmol) (prepared by the route described in Example 1, substituting N-{[(5S)-3-(3,5-difluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide) is dissolved in MeOH (2 mL). To this mixture is added Et3N (0.125 ml, 0.9 mmol) and N′-[(1E)-2,2-dichloroethylidene]-4-methylbenzenesulfonohydrazide (0.17 g, 0.6 mmol)(Prepared in Example 26 step 1). The reaction is stirred at 0° C. to RT for 16 hours. The mixture was concentrated to dryness, reconstituted in CH2Cl2 (125 mL) and extracted with H2O. The organic layer was dried (MgSO4), loaded onto a SIM and purified on a Biotage 12M column to yield (0.033 g, 30%). 1H-NMR (DMSO) δ: 8.17, 7.77, 7.61, 7.25, 5.16, 4.83, 4.21, 3.87, 3.28, 3.18, 2.29, 1.86

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. extractionextracted with H2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. custompurified on a Biotage 12M column
  5. customto yield (0.033 g, 30%)

Sources & evidence

ORD record
ord-38f98b5e5d954dd4aefeef4cc01d73b6
Source dataset
uspto-grants-2006_08
Patent number
US07094900B2

Reaction notes

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