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

HRID 1005849Notes

Reaction equation

HRID 1005849 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-aecb078866ae48eb980ec460f4e4661a
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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