Pyridine → 5-(S)-Thioacetamidomethyl-3-[4'-acetamido-3'-fluorophenyl]oxazolidine-2-one

HRID 351867Notes

Reaction equation

HRID 351867 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)(=[S:3])[CH3:2].[C:20](OC(=O)C)(=[O:22])[CH3:21].N1C=CC=CC=1>ClCCl>[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]([NH:18][C:20](=[O:22])[CH3:21])=[C:14]([F:19])[CH:13]=2)[CH2:7]1)(=[S:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 599058535-(S)-Thioacetamidomethyl-3-[4'-amino-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 599058705-(S)-Thioacetamidomethyl-3-[4'-acetamido-3'-fluorophenyl]oxazolidine-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(S)-thioacetamidomethyl-3-[4′-amino-3′-fluorophenyl]oxazoli-dine-2-one (0.070 g, 0.247 mmol), acetic anhydride (0.25 mL), pyridine (0.38 mL), and dichloromethane (0.75 mL) was stirred at r.t. for 4 h. Solvent was removed under vacuum and the crude product purified by PTLC (10% MeOH in DCM) to give a white solid (0.076 g, 95%). M.p. 200-1° C.; MS (m/z): (M+H)+=326.

Workup

  1. customSolvent was removed under vacuum
  2. customthe crude product purified by PTLC (10% MeOH in DCM)

Sources & evidence

ORD record
ord-4bd029cfa5d84b038b6db8a996a84bf8
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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