Methanol → (5R)-3-[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one

HRID 1452597Notes

Reaction equation

HRID 1452597 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20]O)[O:17][C:16]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([S:13][CH3:14])[N:10]=[N:9]1.[CH3:23][C:24]1[N:25]=[N:26][NH:27][N:28]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.CO>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][N:26]3[N:27]=[N:28][C:24]([CH3:23])=[N:25]3)[O:17][C:16]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([S:13][CH3:14])[N:10]=[N:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1381075-methyl-2H-tetrazoleHCID 57526965(5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one2×

Product 1

HCID 10023271(5R)-3-[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-oneYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one (Intermediate 48) (1.10 g, 3.39 mmol), 5-methyl-2H-tetrazole (0.347 g, 4.09 mmol), polystyrene-triphenylphosphine (phosphine loading 1.51 mmol/g, 3.79 g, 5.72 mmol) and diisopropyl azodicarboxylate (0.856 g, 4.11 mmol) were reacted as described for Example 29 to afford the title product (0.632 g) after chromatography on silica gel with 5% methanol in dichloromethane. The regioisomeric product (5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-[(5-methyl-1H-tetrazol-1-yl)methyl]-1,3-oxazolidin-2-one was also isolated (0.369 g).

Sources & evidence

ORD record
ord-1524e637b17f4b938c66a371ce8c550b
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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