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

HRID 1452596
Notes
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Reaction equation

HRID 1452596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19]O)[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]1.[CH3:22][C:23]1[N:24]=[N:25][NH:26][N:27]=1.CO>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:25]3[N:26]=[N:27][C:23]([CH3:22])=[N:24]3)[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 1381075-methyl-2H-tetrazoleHCID 57526994(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one2×

Product 1

HCID 10089750(5R)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-oneYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

This compound was prepared from (5R)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one (Intermediate 19) (1.054 g, 3.61 mmol) and 5-methyl-2H-tetrazole (0.608 g, 7.23 mmol), as described for Example 29. Chromatography on silica gel with 5% methanol in dichloromethane gave the crude product (0.72 g) which was purified further by trituration with dichloromethane and diethyl ether to afford the title product (0.571 g). The regioisomeric product (5R)-3-[3-fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-[(5-methyl-1H-tetrazol-1-yl)methyl]-1,3-oxazolidin-2-one was also isolated (0.228 g).

Workup

  1. customwas purified further by trituration with dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-7780d2add0bb48e793e385b93583c101
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes