p-Toluenesulfonic acid → (S)-5-(aminomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one

HRID 1484703Notes

Reaction equation

HRID 1484703 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[CH:12]=2)[CH2:6]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[NH2:1][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[CH:12]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11776TriphenylphosphineHCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 58721926(S)-5-(aminomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In Ar atmosphere, (R)-5-(azidomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one (3 g, 8.3 mmol) was dissolved in THF (20 mL) solution, and was added with PPh3 (2.2 g, 8.3 mmol) and p-TsOH (3.2 g, 16.6 mmol). The mixture was agitated at a room temperature for 4 hours, and the solid was filtered and washed with THF, to obtain p-toluenenesulfonic acid salt of (S)-5-(aminomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one (1.5 g, 54%). The product was used for subsequent step.

Workup

  1. filtrationthe solid was filtered
  2. washwashed with THF

Sources & evidence

ORD record
ord-64a64c3b4d364372ab99a2b68c1b3b50
Source dataset
uspto-grants-2016_08
Patent number
US09422274B2

Reaction notes

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