Dimethylformamide → 4-[(5S)-5-[(ethanethioylamino)methyl]-2-oxo-oxazolidin-3-yl]-2-fluoro-benzamide

HRID 351873Notes

Reaction equation

HRID 351873 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]([C:15]([NH2:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1.C(N(CC)CC)C.[C:26](SCC)(=[S:28])[CH3:27].CN(C=O)C>C(#N)C>[C:26]([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]([C:15]([NH2:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1)(=[S:28])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 229661984-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-benzamide

Product 1

HCID 30064334-[(5S)-5-[(ethanethioylamino)methyl]-2-oxo-oxazolidin-3-yl]-2-fluoro-benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(S)-aminomethyl-3-[4′-aminocarbonyl-3′-fluorophenyl]oxazolidine-2-one (1.75 g, 6.9 mmol), triethylamine (2.0 ml, 13.8 mmol) and ethyl dithioacetate (0.87 ml, 7.6 mmol) and DMF (5 ml) in acetonitrile (5 ml) was stirred at r.t. for 48 h. Solvent was removed under vacuum, and the crude material purified by silica gel chromatography (eluent: 10% methanol in ethyl acetate). White crystalline solid (1.3 g, 61%). HPLC Rt=4.5 min. MS (m/z): [M+H]+=312.

Workup

  1. customSolvent was removed under vacuum
  2. customthe crude material purified by silica gel chromatography (eluent: 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-316b602e5ef6489ab036878ce210de8d
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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