HCID 14649523, compound → HCID 14649525, compound

HRID 232121Notes

Reaction equation

HRID 232121 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH2:20][CH2:21]Cl)[O:13][C:12]1([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1C=CC=CC=1.CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[C@H:14]([CH:20]=[CH2:21])[O:13][C:12]1([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14649523HCID 14649523, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14649525HCID 14649525, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

610 mg of (4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-5-(2-chloroethyl)-4-isobutyloxazolidine was dissolved in 3.6 ml of dry benzene, and a solution prepared by dissolving 390 mg of potassium tert-butoxide in 3.6 ml of dimethyl sulfoxide, was added thereto. The mixture was reacted at room temperature for 10 minutes. The reaction solution thus obtained was purified by silica gel column chromatography (packed with 36 g of silica gel, developer: benzene/ethyl acetate (30/1)), and the fraction containing the desired compound was collected and concentrated. The residue thus obtained was dried under reduced pressure to obtain 540 mg (yield: 99%) of (4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-5-ethenyl-4-isobutyloxazolidine as a colorless transparent syrup having the following physical properties.

Workup

  1. customa solution prepared
  2. additionwas added
  3. customThe mixture was reacted at room temperature for 10 minutes
  4. customThe reaction solution thus obtained
  5. customwas purified by silica gel column chromatography (packed with 36 g of silica gel, developer: benzene/ethyl acetate (30/1))
  6. additionthe fraction containing the desired compound
  7. customwas collected
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-2681ffbcba474e329a835516b5fa7468
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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