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

HRID 1452577Notes

Reaction equation

HRID 1452577 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19][N:20]=[N+]=[N-])[O:16][C:15]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][C:10](C)=[N:9]1.N[CH2:25][C@@H]1OC(=O)N(C2C=CC(N3C=C(C)N=N3)=C(F)C=2)C1.CO>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19][NH2:20])[O:16][C:15]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][N:11]([CH3:25])[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 57526957(5S)-5-(Aminomethyl)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-oneHCID 765562153-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one2×

Product 1

HCID 775638193-[3-Fluoro-4-(4-methyl-1,2,4-triazol-1-yl)phenyl]-5-(aminomethyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one (Intermediate 24) (1.8 g, 5.67 mmol) was hydrogenated as described for Intermediate 16. Chromatography on silica gel with 3-7% methanol in dichloromethane gave the title compound (1.28 g).

Sources & evidence

ORD record
ord-088d650f84784044a5be4a5d8c7dca16
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

Loading…