Lithium Chloride → ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate

HRID 1651018Notes

Reaction equation

HRID 1651018 reaction equation
[Cl-].[Li+].C(OP([CH:11]([CH:17]([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH2:42]([O:49][C:50]([N:52]1[C@@H:56]([CH2:57][CH:58]([CH3:60])[CH3:59])[C@H:55]([CH:61]=O)[O:54][C:53]1([CH3:64])[CH3:63])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1>[CH2:42]([O:49][C:50]([N:52]1[C@@H:56]([CH2:57][CH:58]([CH3:59])[CH3:60])[C@H:55]([CH:61]=[C:11]([CH:17]([CH3:18])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:54][C:53]1([CH3:63])[CH3:64])=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 11777661Ethyl 2-(diethoxyphosphoryl)-3-methylbutanoateHCID 14649485(4S,5R)-3-benzyloxycarbonyl-2,2-dimethyl-5-formyl-4-isobutyloxazolidineHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 70045745ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

123 mg of lithium chloride was suspended in 10 ml of dry tetrahydrofuran under an argon atmosphere, and 0.69 ml of ethyl 2-diethylphosphono-3-methylbutanoate was added thereto under stirring. Then, 2.7 ml of a 20% dry tetrahydrofuran solution of diazabicycloundecene was added thereto and stirred for 10 minutes at room temperature. A solution prepared by dissolving 773 mg of (4S,5R)-3-benzyloxycarbonyl-2,2-dimethyl-5-formyl-4-isobutyloxazolidine in dry tetrahydrofuran was gradually dropwise added thereto, and the mixture was stirred overnight at room temperature. The inorganic salt precipitated was filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in 300 ml of benzene, washed with water and dried oer anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (32 g of Kiesel gel 60) by using a mixture of n-hexane/ethyl acetate (10/1) to obtain 623 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate as a colorless oily substance.

Workup

  1. stirringstirred for 10 minutes at room temperature
  2. customA solution prepared
  3. additionwas gradually dropwise added
  4. stirringthe mixture was stirred overnight at room temperature
  5. customThe inorganic salt precipitated
  6. filtrationwas filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe residue was dissolved in 300 ml of benzene
  9. washwashed with water
  10. dry with materialdried oer anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (32 g of Kiesel gel 60)
  13. additiona mixture of n-hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-79c6ecd62a0b4015b321cc9ff1a2b6b7
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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