Sodium Fluoride → (S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

HRID 324564Notes

Reaction equation

HRID 324564 reaction equation
[C:1](SCC)(=[S:3])[CH3:2].[F-].[Na+].[F:9][C:10]1[CH:11]=[C:12]([N:24]2[CH2:28][C@H:27]([CH2:29][NH2:30])[O:26][C:25]2=[O:31])[CH:13]=[CH:14][C:15]=1[CH:16]1[CH2:21][CH2:20][S:19](=[O:23])(=[O:22])[CH2:18][CH2:17]1.[OH-].[K+]>C(O)C.C(Cl)Cl>[F:9][C:10]1[CH:11]=[C:12]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:1](=[S:3])[CH3:2])[O:26][C:25]2=[O:31])[CH:13]=[CH:14][C:15]=1[CH:16]1[CH2:17][CH2:18][S:19](=[O:22])(=[O:23])[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 5235Sodium Fluoride2×HCID 14797Potassium Hydroxide2×HCID 70093Ethyl dithioacetate2×HCID 54349937(5S)-(-)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone

Product 1

HCID 57276083(S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl dithioacetate (100 mL, 0.876 mmol) and sodium fluoride (37 mg, 0.876 mmol) in ethanol (8.8 mL) under a nitrogen atmosphere was treated with a mixture of (S)-(−)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone, as prepared in Step 1, (300 mg, 0.876 mmol) and aqueous potassium hydroxide (1M, 0.88 mL) in ethanol (43.8 mL). The resulting mixture was stirred at ambient temperature for 26 hours, during which additional ethyl dithioacetate (50 mL, 0.438 mmol), sodium fluoride (19 mg, 0.438 mmol), aqueous potassium hydroxide (1M, 0.44 mL) and ethanol (3.0 mL) was added, and was then diluted with methylene chloride (150 mL), washed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was recrystallized from methylene chloride/diethyl ether to give the title compound, mp 186-187° C. (dec.).

Workup

  1. additionwas added
  2. washwashed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-b7852c902aa6435d8264f2223b10f8b3
Source dataset
uspto-grants-2001_04
Patent number
US06218413B1

Reaction notes

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