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

HRID 725587
Notes
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Reaction equation

HRID 725587 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 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-bromomethylnaphthalene 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-820995c68ef4406f8ec3af31e0ecfae4
Source dataset
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05705658

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes