Hydrochloric Acid → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

HRID 843288Notes

Reaction equation

HRID 843288 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:10]([OH:17])[CH2:11]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C(OCC)(=O)C.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:10]1[O:17][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10904464N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

Product 1

HCID 9813904tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methanesulfonyloxybutane(the 2-hydroxy-1-sulfonate compound:the 1-hydroxy-2-sulfonate compound:the diol compound:the 1,2-disulfonate compound=97.1:0.1:0.4:2.3 according to the HPLC area ratio) 50 g dissolved in ethyl acetate 510 ml was added 28% sodium methylate methanol solution 58.2 g under ice-cooling and stirred for 10 min. The reaction solution was diluted with water and adjusted with 6N-HCl to pH7 to separate an organic phase, which was distilled to remove the solvent. The concentrated residue was mixed with n-heptane, stirred at the ambient temperature for 1 hr to deposit crystals, which were filtered to remove. The filtrate was washed with water to separate an organic phase, which was mixed with active charcoal 2 g, stirred at the ambient temperature for 1 hr and filtered to remove charcoal. The filtrate was cooled down to −20° C. to deposit crystals, which were filtered and dried in vacuum to obtain the N-tert-butoxycarbonyl-3(S)-amino-1,2(R)-epoxy-4-phenylbutane(98.5% according to the HPLC area ratio) 28.8 g. The diol compound and the 1,2-disulfonate compound contained in a concentration of 0.5% or less in the crystals according to the HPLC area ratio respectively.

Workup

  1. temperaturecooling
  2. customto separate an organic phase, which
  3. distillationwas distilled
  4. customto remove the solvent
  5. additionThe concentrated residue was mixed with n-heptane
  6. stirringstirred at the ambient temperature for 1 hr
  7. filtrationwere filtered
  8. customto remove
  9. washThe filtrate was washed with water
  10. customto separate an organic phase, which
  11. additionwas mixed with active charcoal 2 g
  12. stirringstirred at the ambient temperature for 1 hr
  13. filtrationfiltered
  14. customto remove charcoal
  15. filtrationwere filtered
  16. customdried in vacuum

Sources & evidence

ORD record
ord-8cc8f15475064303919a0dbca3dc2086
Source dataset
uspto-grants-2002_04
Patent number
US06376685B1

Reaction notes

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