Methylethylenethiourea → (5R)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(3-methyl-2-thioxo-2,3-dihydroimidazol-1-ylmethyl)oxazolidin-2-one

HRID 723780Notes

Reaction equation

HRID 723780 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18]OS(C)(=O)=O)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.[CH3:26][N:27]1[CH2:31][CH2:30][NH:29][C:28]1=[S:32]>>[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:29]4[CH:30]=[CH:31][N:27]([CH3:26])[C:28]4=[S:32])[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 2733224MethylethylenethioureaHCID 213566765(R)-methanesulfonyloxymethyl 3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one

Product 1

HCID 86590236(5R)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(3-methyl-2-thioxo-2,3-dihydroimidazol-1-ylmethyl)oxazolidin-2-oneYield 9.2%

Procedure

Essentially the procedure of Example 37 was used, but starting with (5R)-3-(4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (300 mg, 0.81 mM), and 1-methylimidazolidin-2-thione (100 mg, 0.88 mM) and heating the reaction at 60° for 1.5 hours. Chromatography on two columns gave the desired product (29 mg).

Workup

  1. temperatureheating
  2. customthe reaction at 60° for 1.5 hours

Sources & evidence

ORD record
ord-1f003cb055a749f39526407e422ec0d1
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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