Tetrafluoro-m-phenylenediamine dihydrochloride → (5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

HRID 1472496Notes

Reaction equation

HRID 1472496 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH:34]C(C3C=CC=CC=3)C)[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][C@H:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][C@@H:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 902170523-(3-Fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one2×

Product 2

HCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinoneHCID 11500308Deacetyl (R)-Linezolid

Procedure

The procedure is the same as in Example 41 except that the dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one (4a) was replaced by the corresponding 3-(3-fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one (4c-4h) to give 3-(3-fluoro-4-morpholinylphenyl)-5(S)-aminomethyl-1,3-oxazolidin-2-one ((S)-5b) or 3-(3-fluoro-4-morpholinylphenyl)-5(R)-aminomethyl-1,3-oxazolidin-2-one ((R)-5b).

Sources & evidence

ORD record
ord-f657708320014b9e85af047402b1caad
Source dataset
uspto-grants-2015_04
Patent number
US09012631B2

Reaction notes

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