Triethylamine → 5-(S)-Thioacetamidomethyl-3-[4'-(N-hydroxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 2305665Notes

Reaction equation

HRID 2305665 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]([NH:17][O:18]C)=[O:16])=[C:11]([F:20])[CH:10]=2)[CH2:4]1.C(N(CC)CC)C.[C:28](SCC)(=[S:30])[CH3:29]>CN(C=O)C>[C:28]([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]([NH:17][OH:18])=[O:16])=[C:11]([F:20])[CH:10]=2)[CH2:4]1)(=[S:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 229662015-(S)-Aminomethyl-3-[4'-(N-methoxyamino)carbonvl-3'-fluorophenyl]-oxazolidine-2-one

Product 1

HCID 865863915-(S)-Thioacetamidomethyl-3-[4'-(N-hydroxyamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(S)-aminomethyl-3-[4′-(N-methoxyamino)carbonyl-3′-fluorophenyl]-oxazolidine-2-one (0.053 ml, 0.47 mmol), triethylamine (0.12 ml, 0.84 mmol) and ethyl dithioacetate (0.87 ml, 7.6 mmol) in DMF (0.75 ml) was stirred at r.t. for 48 h. Solvent was removed under vacuum, and the crude material purified by silica gel PTLC (eluent: 5% MeOH in ethyl acetate). White crystalline solid (100 mg, 70%). HPLC Rt=4.6 min. MS (m/z): [M+H]+=342.

Workup

  1. customSolvent was removed under vacuum
  2. customthe crude material purified by silica gel PTLC (eluent: 5% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-312da85ae716486f8292b8c3cda4996b
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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