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

HRID 351890Notes

Reaction equation

HRID 351890 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]([CH2:17][CH3:18])=[O:16])=[C:11]([F:19])[CH:10]=2)[CH2:4]1.[C:20](SCC)(=[S:22])[CH3:21]>CN(C=O)C>[C:20]([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]([CH2:17][CH3:18])=[O:16])=[C:11]([F:19])[CH:10]=2)[CH2:4]1)(=[S:22])[CH3:21]

Participants

4

Reactant 2

HCID 70093Ethyl dithioacetateHCID 229661995-(S)-Aminomethyl-3-[4'-ethylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 99281065-(S)-Thioacetamidomethyl-3-[4'-ethylsulfinyl-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′-ethylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.0885 g, 0.309 mmol) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0.104 g (98%). M.p. 138-9° C. MS (m/z): [M+H]+=345.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-4a66ff8d612f461bb857e7a9033e4dc2
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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