Ethylbenzene → (2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane

HRID 651257Notes

Reaction equation

HRID 651257 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:10]([OH:13])[CH2:11]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O-:24])(=[O:23])[CH3:22].[K+].C(C1C=CC=CC=1)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:21]([O:24][CH2:11][C@@H:10]([OH:13])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 7500EthylbenzeneHCID 517044Potassium AcetateHCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

Product 1

HCID 11056398(2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutaneYield 45%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture composed of 2.0 mmol (0.599 g) of (2S,3S)-3-(t-butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane, 0.1 mmol (0.032 g) of tetrabutylammoniumbromide, 5.0 mmol (0.49 g) of potassium acetate and 10 ml of acetonitrile was stirred under reflux for 50 hours. Thereafter, the solvent was distilled off under reduced pressure, 20 ml of water and 20 ml of ethyl acetate were added, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. Quantitative analysis was curried out by high performance liquid chromatography using ethylbenzene as an internal standard. Thus was obtained 0.289 g (45%) of the title compound.

Workup

  1. temperatureunder reflux for 50 hours
  2. distillationThereafter, the solvent was distilled off under reduced pressure, 20 ml of water and 20 ml of ethyl acetate
  3. additionwere added
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a crude product

Sources & evidence

ORD record
ord-bf3a26b2fc394a9b81216f832935b558
Source dataset
uspto-grants-2001_08
Patent number
US06278002B1

Reaction notes

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