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

HRID 2305682Notes

Reaction equation

HRID 2305682 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][CH2:18][F:19])=[O:16])=[C:11]([F:20])[CH:10]=2)[CH2:4]1.[C:21](SCC)(=[S:23])[CH3:22]>CN(C=O)C>[C:21]([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][CH2:18][F:19])=[O:16])=[C:11]([F:20])[CH:10]=2)[CH2:4]1)(=[S:23])[CH3:22]

Participants

4

Reactant 2

HCID 70093Ethyl dithioacetateHCID 599058715-(S)-Aminomethyl-3-[4'-(2''-fluoroethyl)sulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 98637885-(S)-Thioacetamidomethyl-3-[4'-(2''-fluoroethyl)sulfinyl-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′-(2″-fluoroethyl)sulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.100 g, 0.329 mmol) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0.114 g (96%). M.p. 161° C. MS (m/z): [M+H]+=363.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-e39c72632ba545ed9ff8b44d62a4f170
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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