Ammonium Chloride → 3-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

HRID 264889Notes

Reaction equation

HRID 264889 reaction equation
[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])(=[O:5])[CH2:2][CH2:3][CH3:4].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:29]([O:32][CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36]([CH2:44]Br)[CH:35]=1)[CH2:30][CH3:31].[Cl-].[NH4+]>O1CCCC1>[CH2:3]([C@@H:2]([CH2:44][C:36]1[CH:35]=[C:34]([CH2:33][O:32][CH2:29][CH2:30][CH3:31])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11736739(4R)-4-benzyl-3-butanoyl-1,3-oxazolidin-2-oneHCID 214587034-Propoxymethyl-2-bromomethylnaphthalene

Product 1

HCID 228657673-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-75 °C

Procedure

30 ml of tetrahydrofuran and a solution of 2.97 g of 3-butyroyl-4(R)-benzyl-oxazolidin-2-one in 15 ml of tetrahydrofuran are added dropwise in succession to a solution, stirred at -75° C., of 12 ml of 1M lithium hexamethyldisilazide solution. The reaction mixture is stirred for 1 hour at -75° C., a solution of 3.52 g of 4-propoxymethyl-2-bromomethyl-naphthalene in 15 ml of tetrahydrofuran is added dropwise thereto and the mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C. After the dropwise addition at 0° C. of 2.7 ml of saturated ammonium chloride solution, the reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and water. The organic extracts are concentrated by evaporation and the residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1), yielding the title compound: Rf (dichloromethane/hexane=3:1)=0.24; FAB-MS (M+Na)+ =482.

Workup

  1. stirringthe mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. customthe residue is partitioned between diethyl ether and water
  4. concentrationThe organic extracts are concentrated by evaporation
  5. customthe residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1)

Sources & evidence

ORD record
ord-4909a452e937443aa8ecf5191cfb1302
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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