Benzaldehyde → (4S)-3-[(2R)-2-Benzyl-(3R)-3-hydroxy-3-phenylpropionyl]-4-(2-propyl)-oxazolidin-2-one

HRID 4941Notes

Reaction equation

HRID 4941 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].[C:21]1([CH2:27][CH2:28][C:29]([N:31]2[C@@H:35]([CH:36]([CH3:38])[CH3:37])[CH2:34][O:33][C:32]2=[O:39])=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH:40](=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)C>[CH2:27]([C@H:28]([C@@H:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:29]([N:31]1[C@@H:35]([CH:36]([CH3:37])[CH3:38])[CH2:34][O:33][C:32]1=[O:39])=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 6

HCID 240BenzaldehydeHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 10467835(S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 15714137(4S)-3-[(2R)-2-Benzyl-(3R)-3-hydroxy-3-phenylpropionyl]-4-(2-propyl)-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.55 ml (11 mmol) of diisopropylamine is dissolved in 20 ml of absolute THF under argon and 7.75 ml (12 mmol) of n-butyllithium solution (1.55M in n-hexane, Aldrich) are added at -20° C. with stirring. The mixture is stirred at this temperature for 10 minutes and the freshly prepared solution of lithium diisopropylamide prepared in this way is then added dropwise to a solution of 2.61 g (10 mmol) of (4S)-3-(3-phenylpropionyl)-4-(2-propyl)-oxazolidin-2-one (J.J. Plattner et al., J. Med. Chem. 1988, 31 (12), 2277-2288) cooled to -70° C. in 30 ml of absolute THF. The mixture is subsequently stirred at -70° C. for 30 minutes and 1.32 ml (13 mmol) of benzaldehyde are injected into the mixture via a septum. After one hour at this temperature, the mixture is hydrolyzed by adding 100 ml of saturated ammonium chloride solution and allowed to come to room temperature, and 100 ml of diethyl ether are added. The organic phase is separated off and the aqueous phase is extracted with 100 ml of diethyl ether.

Workup

  1. stirringThe mixture is stirred at this temperature for 10 minutes
  2. stirringThe mixture is subsequently stirred at -70° C. for 30 minutes
  3. customto come to room temperature
  4. customThe organic phase is separated off
  5. extractionthe aqueous phase is extracted with 100 ml of diethyl ether

Sources & evidence

ORD record
ord-9e0c26d35a4d43579f5bc9ade572d92d
Source dataset
uspto-grants-1993_09
Patent number
US05242903

Reaction notes

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