(5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-one → (5S)-3-{4-[4-(tert-Butyl(dimethyl)silyloxymethyl)-1H-imidazol-1-yl]-3-fluorophenyl}-5-(aminomethyl)oxazolidin-2-one

HRID 1452585Notes

Reaction equation

HRID 1452585 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][N:27]=[N+]=[N-])[O:23][C:22]3=[O:30])=[CH:17][C:16]=2[F:31])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].NC[C@@H]1OC(=O)N(C2C=CC(N3C=C(C)N=N3)=C(F)C=2)C1>>[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH2:27])[O:23][C:22]3=[O:30])=[CH:17][C:16]=2[F:31])[CH:14]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 57114338(5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-oneHCID 57526957(5S)-5-(Aminomethyl)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one

Product 1

HCID 57527007(5S)-3-{4-[4-(tert-Butyl(dimethyl)silyloxymethyl)-1H-imidazol-1-yl]-3-fluorophenyl}-5-(aminomethyl)oxazolidin-2-oneYield 102.6%

Procedure

(5R)-3-{4-[4-(tert-Butyl(dimethyl)silyloxymethyl)-1H-imidazol-1-yl]-3-fluorophenyl}-5-(azidomethyl)oxazolidin-2-one (WO 9928317, WO 9910343, WO 9731917) (2.0 g, 4.17 mmol) was reacted as described for Intermediate 16 to give the title compound (1.8 g) as a solid, which was taken to the next step without further purification.

Sources & evidence

ORD record
ord-a94102ff3459480291e1dc03937beb79
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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