Ammonium Chloride → 4-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2one

HRID 992424Notes

Reaction equation

HRID 992424 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[O:29]1[CH2:34]CCOO1.[Cl-].[NH4+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@@H:15]([CH2:34][OH:29])[CH:16]([CH3:17])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 11391340(4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-oneHCID 19593658CID 19593658

Product 1

HCID 228882854-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2oneYield 124.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride (18 ml) was added dropwise to a solution of 4-(R)-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (41.5 g) in dichloromethane (300 ml) at 0° C. Diisopropylethylamine (28 ml) was added dropwise and the resulting purple suspension was stirred for 30 min, then a solution of trioxane (11.2 g) was added, followed by titanium tetrachloride (18 ml) and the mixture was stirred for two hours, during which time the solution changed in colour from purple to amber. Ammonium chloride (400 ml saturated aqueous solution) was added and the mixture was stirred for 10 min, then the phases separated and the organic layer washed with water and saturated brine, dried (Na2SO4) and evaporated to give the title compound as a colourless solid (45 g).

Workup

  1. stirringthe mixture was stirred for two hours, during which time the solution
  2. stirringthe mixture was stirred for 10 min
  3. customthe phases separated
  4. washthe organic layer washed with water and saturated brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a1bf337185d64fb8b33d702dea570f29
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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