Lawesson's reagent → 5-(S)-Thioacetamidomethyl-3-[4'-amino-3'-fluorophenyl]oxazolidine-2-one

HRID 351866Notes

Reaction equation

HRID 351866 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:19])[CH:13]=2)[CH2:7]1)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>O1CCOCC1>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:19])[CH:13]=2)[CH2:7]1)(=[S:29])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10778218(S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 599058535-(S)-Thioacetamidomethyl-3-[4'-amino-3'-fluorophenyl]oxazolidine-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-(S)-acetamidomethyl-3-[4′-amino-3′-fluorophenyl]oxazoli-dine-2-one. (0.100 g, 0.374 mmol) and Lawesson's reagent (0.151 g, 0.374 mol) in dioxane (2 ml) was stirred at 65° C. for 2 h. The solution was concentrated under vacuum and the residue purified by PTLC (10% methanol/dichloromethane) to give a tan solid (0.104 g, 98%); mp 137-88° C.; MS: (M+H)+=284.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue purified by PTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-071b10134f52488eb9d160097d98afd8
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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