Ammonium Chloride → 3-[2(R)-isopropyl-3(p-tert-butyl-phenyl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

HRID 2258294Notes

Reaction equation

HRID 2258294 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[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:30]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[C@H:15]([CH2:38][C:37]1[CH:40]=[CH:41][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=1)[CH:16]([CH3:17])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 2733832Lithium HexamethyldisilazideHCID 11391340(4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-one

Product 1

HCID 228657663-[2(R)-isopropyl-3(p-tert-butyl-phenyl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-70 °C

Procedure

A solution of 4(R)-benzyl-3-isovaleroyl-oxazolidin-2-one (13.2 g) in tetrahydrofuran (20 ml) is added dropwise under an inert atmosphere, with stirring, at -70° C. to a 1M lithium hexamethyldisilazide solution in tetrahydrofuran (31 ml) which has been diluted with tetrahydrofuran (30 ml), and the reaction mixture is stirred at -70° C. for 1 hour. A solution of p-tert-butyl-benzyl bromide (9.6 g) in tetrahydrofuran (20 ml) is then added dropwise and the mixture is stirred for a further one hour at -25° C. and for 4 hours at 0° C. 6 ml of a saturated ammonium chloride solution are added to the reaction mixture which is then freed of tetrahydrofuran by concentration under reduced pressure and extracted with diethyl ether. The title compound is obtained from the residue of the extract by purification by means of FC (700 g of silica gel, eluant dichloromethane/hexane 1:1): Rf (dichloromethane/hexane 1:1)=0.30; m.p. 123.5°-124° C.

Workup

  1. stirringthe mixture is stirred for a further one hour at -25° C. and for 4 hours at 0° C
  2. concentrationis then freed of tetrahydrofuran by concentration under reduced pressure
  3. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-47a922455fda446187383d7c2e67ebed
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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