4-Toluenesulfonyl chloride → HCID 14681747, compound

HRID 232120Notes

Reaction equation

HRID 232120 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][OH:22])[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.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[C@H:14]([CH2:20][CH2:21][O:22][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[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

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14649521HCID 14649521, compound

Product 1

HCID 14681747HCID 14681747, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.89 g of (4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-5-(2-hydroxyethyl)-4-isobutyloxazolidine was dissolved in 15 ml of pyridine, and 2.65 g of p-toluenesulfonyl chloride was added and dissolved therein. The mixture was then reacted at room temperature overnight. The reaction solution thus obtained was concentrated, and precipitated insolubles were filtered off. The filtrate thus obtained was purified by silica gel column chromatography (developer: benzene/ethyl acetate (30/1)) to obtain 4.47 g of (4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-5-(2-p-toluenesulfonyloxyethyl)-4-isobutyloxazolidine as a syrup.

Workup

  1. dissolutiondissolved
  2. customThe mixture was then reacted at room temperature overnight
  3. customThe reaction solution thus obtained
  4. concentrationwas concentrated
  5. customprecipitated insolubles
  6. filtrationwere filtered off
  7. customThe filtrate thus obtained
  8. customwas purified by silica gel column chromatography (developer: benzene/ethyl acetate (30/1))

Sources & evidence

ORD record
ord-d050524fa7a64297bc9de3ba26710daf
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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