Ammonium Chloride → HCID 14989076, compound

HRID 2380121Notes

Reaction equation

HRID 2380121 reaction equation
[CH2:1]([Li])CCC.[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1)([CH3:8])[CH3:7].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](Cl)=[O:26])=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[N:10]1[C:25](=[O:26])[CH2:24][CH:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[CH3:1])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 109324413-(4-Methoxyphenyl)propionyl chlorideHCID 178418339Butyllithium

Product 1

HCID 14989076HCID 14989076, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

18.19 ml (29.1 mmoles) of butyllithium (as a 1.6M hexane solution) were added dropwise at -78° C. and under an atmosphere of nitrogen to a solution of 3.13 g (24.2 mmoles) of 4(S)-isopropyl-2-oxazolidinone in 50 ml of anhydrous tetrahydrofuran, and then the mixture was stirred for 30 minutes. At the end of this time, a solution of 5.43 g (29.1 mmoles) of 3-(4-methoxyphenyl)propionyl chloride in 20 ml of anhydrous tetrahydrofuran was added dropwise to the resulting mixture over the course of 10 minutes. The mixture was then stirred for a further 1 hour, after which a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by medium pressure silica gel column chromatography (using a 1:3 by volume mixture of ethyl acetate and hexane as eluent), followed by recrystallization from diisopropyl ether, to give 5.63 g (yield 80%) of the title compound as white crystals, melting at 62.0°-63.5° C.

Workup

  1. stirringThe mixture was then stirred for a further 1 hour
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by medium pressure silica gel column chromatography (
  6. additionby volume mixture of ethyl acetate and hexane as eluent),
  7. customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-2fff1a43e5684c94867ca1a878bb732d
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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