Ethyl dithioacetate → 5-(S)-Thioacetamidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

HRID 351886Notes

Reaction equation

HRID 351886 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1.[C:19](SCC)(=[S:21])[CH3:20]>CN(C=O)C>[C:19]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1)(=[S:21])[CH3:20]

Participants

4

Reactant 2

HCID 70093Ethyl dithioacetateHCID 229662005-(S)-aminomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 99494045-(S)-Thioacetamidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to the Method A of General Methods of Preparation of 5-(S)-Thioamidomethyloxazolidinones (Example 1) from 5-(S)-aminomethyl-3-[4′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.050 g, 0.184 mmol) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0.058 g (96%). M.p 158-60° C. MS (m/z): [M+H]+=331.

Workup

  1. customReaction
  2. customM.p 158-60° C

Sources & evidence

ORD record
ord-5b7c04d086f64326b7e370a25e072f20
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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