Water → 4(R)-Benzyl-3-(2(R)-acetylthiomethyl-3-methylbutyryl)oxazolidin-2-one

HRID 393699Notes

Reaction equation

HRID 393699 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([C@@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:19](=[O:26])[CH:20]([CH2:24]I)[CH:21]([CH3:23])[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>CN(C)C=O>[CH2:6]([C@@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:19](=[O:26])[C@H:20]([CH2:24][S:3][C:1](=[O:4])[CH3:2])[CH:21]([CH3:22])[CH3:23])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 228882814(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-oneHCID 23670855Potassium ethanethioate

Product 1

HCID 228882834(R)-Benzyl-3-(2(R)-acetylthiomethyl-3-methylbutyryl)oxazolidin-2-oneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (19 g) was added to a solution of the 4-(R)-benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-one (56 g) in N,N-dimethylformamide (200 ml), and the mixture was stirred for 3 h at room temperature, then poured into water (600 ml). The mixture was extracted with diethyl ether (2×500 ml) and the organic solvent washed with water and saturated brine, dried (Na2SO4) and evaporated to give the title compound as a pale amber oil (48.6 g).

Workup

  1. extractionThe mixture was extracted with diethyl ether (2×500 ml)
  2. washthe organic solvent washed with water and saturated brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6f45890dbd0f4fa8a4228ee370116d7e
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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